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    Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols
    1.
    发明授权
    Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols 有权
    制备O-甲基苯酚，N-甲基杂芳族化合物和甲基化氨基酚的加速方法

    公开(公告)号：US06706929B2

    公开(公告)日：2004-03-16

    申请号：US10459763

    申请日：2003-06-12

    申请人： Wen-Chung Shieh ,  Steven Dell

    发明人： Wen-Chung Shieh ,  Steven Dell

    IPC分类号： C07C4320

    CPC分类号： C07D235/06 ,  C07C41/16 ,  C07D209/08 ,  C07D209/86 ,  C07D235/18 ,  C07C43/2055 ,  C07C43/205

    摘要： An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. The process of the invention is especially advantageous since the process: (1) utilizes an environmentally friendly methylating reagent, dimethylcarbonate; (2) produces a high yield of the O-methyl phenols, N-methyl aromatic amines, and/or methylated aminophenols, generally 97-100% conversion; and (3) does not require a high-pressure (autoclave) reactor.

    摘要翻译： 一种制备O-甲基苯酚的加速方法，包括使苯酚与碳酸二甲酯在选自1,8-二氮杂双环[5.4.0]十一碳-7-烯的催化剂存在下反应; 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 根据另一方面，本发明提供了一种制备N-甲基杂芳族化合物的加速方法，包括使含NH杂芳族化合物与碳酸二甲酯在选自1,8-二氮杂双环[5.4.0]十一碳烯 - 七烯 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 根据另一方面，本发明提供了一种制备甲基化氨基苯酚的加速方法，包括在选自1,8-二氮杂双环[5.4.0]十一碳-7-烯的催化剂存在下使具有至少一个NH的氨基苯酚与碳酸二甲酯反应 烯; 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 本发明的方法是特别有利的，因为该方法：（1）利用环境友好的甲基化试剂，碳酸二甲酯; （2）产生高产率的O-甲基苯酚，N-甲基芳族胺和/或甲基化氨基苯酚，一般为97-100％转化率; 和（3）不需要高压（高压釜）反应器。

    N-alkylation of indole derivatives
    2.
    发明授权
    N-alkylation of indole derivatives 有权
    吲哚衍生物的N-烷基化

    公开(公告)号：US07067676B2

    公开(公告)日：2006-06-27

    申请号：US11009206

    申请日：2004-12-10

    申请人： Steven Dell ,  Mario E Lozanov ,  Wen-Chung Shieh

    发明人： Steven Dell ,  Mario E Lozanov ,  Wen-Chung Shieh

    IPC分类号： C07D209/12

    CPC分类号： C07D209/86 ,  C07D209/08 ,  C07D209/42

    摘要： The present invention provides methods for the efficient preparation of indole derivatives of the formula wherein X is methyl or benzyl; and R1, R2, R3 and R4 are independently hydrogen, halogen, cyano, nitro, hydroxy, optionally substituted alkyl, alkoxy, aralkoxy, carboxy, alkoxycarbonyl, aryl or heteroaryl; or R1 and R2 combined together with the carbon atoms to which they are attached form a fused 6-membered aromatic ring; by reacting indoles of the formula wherein R1, R2, R3 and R4 have meanings as defined for formula I, with dimethyl carbonate when X is methyl, or with dibenzyl carbonate when X is benzyl, in the presence of a catalytic amount of a base at an ambient temperature to afford compounds of formula I wherein X, R1, R2, R3 and R4 have meanings as defined herein above. In particular, the present invention provides methylation and benzylation of the indole nitrogen in nearly quantitative yields using 1,4-diazabicyclo[2.2.2]octane as the base in a catalytic amount under mild conditions, wherein the alkylations may be conducted in the absence or the presence of an ionic liquid, under microwave irradiation or utilizing conventional heat, or combinations thereof.

    摘要翻译： 本发明提供了有效制备下式的吲哚衍生物的方法，其中X是甲基或苄基; R 1，R 2，R 3和R 4独立地是氢，卤素，氰基，硝基， 羟基，任选取代的烷基，烷氧基，芳烷氧基，羧基，烷氧基羰基，芳基或杂芳基; 或R 1和R 2与它们所连接的碳原子一起形成稠合的6元芳族环; 通式为其中R 1，R 2，R 3和R 4的吲哚的含义如下： 对于式I，当X为甲基时为碳酸二甲酯，或当X为苄基时为碳酸二苄酯，在环境温度下，在催化量的碱存在下，得到式I化合物，其中X，R 1， R 3，R 3，R 3和R 4具有如上文所定义的含义。 特别地，本发明在温和条件下以催化量使用1,4-二氮杂双环[2.2.2]辛烷作为碱，以几乎定量的产率提供吲哚氮的甲基化和苄基化，其中烷基化可以在不存在的情况下进行 或离子液体的存在，在微波照射下或利用常规热，或其组合。

    N-alkylation of indole derivatives
    3.
    发明授权
    N-alkylation of indole derivatives 有权
    吲哚衍生物的N-烷基化

    公开(公告)号：US06972336B2

    公开(公告)日：2005-12-06

    申请号：US10620625

    申请日：2003-07-16

    申请人： Steven Dell ,  Mario Emilov Lozanov ,  Wen-Chung Shieh

    发明人： Steven Dell ,  Mario Emilov Lozanov ,  Wen-Chung Shieh

    IPC分类号： C07D209/08 ,  C07D209/42 ,  C07D209/86 ,  C07D209/12

    CPC分类号： C07D209/86 ,  C07D209/08 ,  C07D209/42

    摘要： The present invention provides methods for the efficient preparation of indole derivatives of the formula wherein X is methyl or benzyl; and R1, R2, R3 and R4 are independently hydrogen, halogen, cyano, nitro, hydroxy, optionally substituted alkyl, alkoxy, aralkoxy, carboxy, alkoxycarbonyl, aryl or heteroaryl; or R1 and R2 combined together with the carbon atoms to which they are attached form a fused 6-membered aromatic ring; by reacting indoles of the formula wherein R1, R2, R3 and R4 have meanings as defined for formula I, with dimethyl carbonate when X is methyl, or with dibenzyl carbonate when X is benzyl, in the presence of a catalytic amount of a base at an ambient temperature to afford compounds of formula I wherein X, R1, R2, R3 and R4 have meanings as defined herein above. In particular, the present invention provides methylation and benzylation of the indole nitrogen in nearly quantitative yields using 1,4-diazabicyclo[2.2.2]octane as the base in a catalytic amount under mild conditions, wherein the alkylations may be conducted in the absence or the presence of an ionic liquid, under microwave irradiation or utilizing conventional heat, or combinations thereof.

    摘要翻译： 本发明提供了有效制备下式的吲哚衍生物的方法，其中X是甲基或苄基; R 1，R 2，R 3和R 4独立地是氢，卤素，氰基，硝基， 羟基，任选取代的烷基，烷氧基，芳烷氧基，羧基，烷氧基羰基，芳基或杂芳基; 或R 1和R 2与它们所连接的碳原子一起形成稠合的6元芳族环; 通式为其中R 1，R 2，R 3和R 4的吲哚的含义如下： 对于式I，当X为甲基时为碳酸二甲酯，或当X为苄基时为碳酸二苄酯，在环境温度下，在催化量的碱存在下，得到式I化合物，其中X，R 1， R 3，R 3，R 3和R 4具有如上文所定义的含义。 特别地，本发明在温和条件下以催化量使用1,4-二氮杂双环[2.2.2]辛烷作为碱，以几乎定量的产率提供吲哚氮的甲基化和苄基化，其中烷基化可以在不存在的情况下进行 或离子液体的存在，在微波照射下或利用常规热，或其组合。

    N-alkylation of indole derivatives
    4.
    发明申请
    N-alkylation of indole derivatives 有权

    公开(公告)号：US20050101786A1

    公开(公告)日：2005-05-12

    申请号：US11009206

    申请日：2004-12-10

    申请人： Steven Dell ,  Mario Lozanov ,  Wen-Chung Shieh

    发明人： Steven Dell ,  Mario Lozanov ,  Wen-Chung Shieh

    IPC分类号： C07D209/08 ,  C07D209/42 ,  C07D209/86 ,  A61K31/405 ,  C07D209/52

    CPC分类号： C07D209/86 ,  C07D209/08 ,  C07D209/42

    摘要： The present invention provides methods for the efficient preparation of indole derivatives of the formula wherein X is methyl or benzyl; and R1, R2, R3 and R4 are independently hydrogen, halogen, cyano, nitro, hydroxy, optionally substituted alkyl, alkoxy, aralkoxy, carboxy, alkoxycarbonyl, aryl or heteroaryl; or R1 and R2 combined together with the carbon atoms to which they are attached form a fused 6-membered aromatic ring; by reacting indoles of the formula wherein R1, R2, R3 and R4 have meanings as defined for formula I, with dimethyl carbonate when X is methyl, or with dibenzyl carbonate when X is benzyl, in the presence of a catalytic amount of a base at an ambient temperature to afford compounds of formula I wherein X, R1, R2, R3 and R4 have meanings as defined herein above. In particular, the present invention provides methylation and benzylation of the indole nitrogen in nearly quantitative yields using 1,4-diazabicyclo[2.2.2]octane as the base in a catalytic amount under mild conditions, wherein the alkylations may be conducted in the absence or the presence of an ionic liquid, under microwave irradiation or utilizing conventional heat, or combinations thereof.

    Microwave irradiation process for preparing methyl esters
    5.
    发明授权
    Microwave irradiation process for preparing methyl esters 有权
    微波辐射法制备甲酯

    公开(公告)号：US06653503B2

    公开(公告)日：2003-11-25

    申请号：US10214644

    申请日：2002-08-08

    申请人： Wen-Chung Shieh ,  Steven Dell

    发明人： Wen-Chung Shieh ,  Steven Dell

    IPC分类号： C07C6902

    CPC分类号： C07H9/04 ,  C07C67/11 ,  C07D207/16 ,  C07H7/00 ,  C07C69/92 ,  C07C69/614 ,  C07C69/78 ,  C07C69/80

    摘要： An accelerated process for preparing a methyl ester having formula (III) said process comprising reacting a carboxylic acid or salt thereof having formula (I) with dimethyl carbonate having formula (II) in the presence of a catalyst selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; 4-dimethylaminopyridine; and combinations thereof, wherein R1 is selected from the group consisting of an alkyl, aryl, alkoxy, alkenyl, cycloalkyl, benzocycloalkyl, cycloalkylalkyl, aralkyl, heterocyclic, heteroaralkyl, alkoxyalkyl, carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, and haloalkyl; and M is selected from the group consisting of hydrogen, a monovalent metal, and a monovalent fractional part of a polyvalent metal, wherein said process is conducted under microwave irradiation at a frequency from 300 MHz to 30 GHz, and at a temperature of from about 120° C. to 300° C. for a period of microwave irradiation time from about 1 second to about 300 minutes. The process of the invention is especially advantageous for preparing methyl esters since the process: (1) utilizes an environmentally friendly methylating reagent, dimethylcarbonate; (2) produces a high yield of the methyl ester, generally 95-99% conversion in less than 30 minutes of microwave irradiation; (3) minimizes degradation and/or racemization of optically pure compounds; and (4) minimizes the formation of by-products.

    摘要翻译： 一种制备具有式（III）的甲酯的加速方法，所述方法包括使式（I）的羧酸或其盐与具有式（II）的碳酸二甲酯在选自下列的催化剂存在下反应： 8-二氮杂双环[5.4.0]十一碳-7-烯; 1,4-二氮杂双环[2.2.2]辛烷; 4-二甲基氨基吡啶; 其中R 1选自烷基，芳基，烷氧基，烯基，环烷基，苯并环烷基，环烷基烷基，芳烷基，杂环，杂芳烷基，烷氧基烷基，羧基烷基，烷基羰基，烷氧基羰基，烷氧基羰基烷基和卤代烷基。 并且M选自氢，一价金属和多价金属的一价分数部分，其中所述方法在微波照射下以300MHz至30GHz的频率进行，并且在约 在约1秒至约300分钟之间的微波照射时间为120℃至300℃。 本发明的方法特别有利于制备甲酯，因为该方法：（1）利用环境友好的甲基化试剂，碳酸二甲酯; （2）产生高产率的甲酯，在少于30分钟的微波照射中通常转化率为95-99％; （3）使光学纯化合物的降解和/或外消旋化最小化; 和（4）最小化副产物的形成。

    N-alkylation of indole derivatives
    6.
    发明申请
    N-alkylation of indole derivatives 审中-公开
    吲哚衍生物的N-烷基化

    公开(公告)号：US20050010055A1

    公开(公告)日：2005-01-13

    申请号：US10917058

    申请日：2004-08-12

    申请人： Steven Dell ,  Mario Lozanov ,  Wen-Chung Shieh

    发明人： Steven Dell ,  Mario Lozanov ,  Wen-Chung Shieh

    IPC分类号： C07D209/08 ,  C07D209/42 ,  C07D209/86 ,  C07D209/82 ,  C07D209/04

    CPC分类号： C07D209/86 ,  C07D209/08 ,  C07D209/42

    摘要： The present invention provides methods for the efficient preparation of indole derivatives of the formula wherein X is methyl or benzyl; and R1, R2, R3 and R4 are independently hydrogen, halogen, cyano, nitro, hydroxy, optionally substituted alkyl, alkoxy, aralkoxy, carboxy, alkoxycarbonyl, aryl or heteroaryl; or R1 and R2 combined together with the carbon atoms to which they are attached form a fused 6-membered aromatic ring; by reacting indoles of the formula wherein R1, R2, R3 and R4 have meanings as defined for formula I, with dimethyl carbonate when X is methyl, or with dibenzyl carbonate when X is benzyl, in the presence of a catalytic amount of a base at an ambient temperature to afford compounds of formula I wherein X, R1, R2, R3 and R4 have meanings as defined herein above. In particular, the present invention provides methylation and benzylation of the indole nitrogen in nearly quantitative yields using 1,4-diazabicyclo[2.2.2]octane as the base in a catalytic amount under mild conditions, wherein the alkylations may be conducted in the absence or the presence of an ionic liquid, under microwave irradiation or utilizing conventional heat, or combinations thereof.

    摘要翻译： 本发明提供了有效制备下式的吲哚衍生物的方法，其中X是甲基或苄基; R 1，R 2，R 3和R 4独立地是氢，卤素，氰基，硝基，羟基，任选取代的烷基，烷氧基，芳烷氧基，羧基，烷氧基羰基，芳基或杂芳基; 或者R 1和R 2与它们所连接的碳原子一起形成稠合的6元芳族环; 通过使式R 1，R 2，R 3和R 4具有如式I定义的含义的吲唑与X为甲基时的碳酸二甲酯反应，或当X为苄基时与碳酸二苄酯反应，在催化量的碱存在下， 环境温度以得到式I化合物，其中X，R 1，R 2，R 3和R 4具有如上文所定义的含义。 特别地，本发明在温和条件下以催化量使用1,4-二氮杂双环[2.2.2]辛烷作为碱，以几乎定量的产率提供吲哚氮的甲基化和苄基化，其中烷基化可以在不存在的情况下进行 或离子液体的存在，在微波照射下或利用常规热，或其组合。

    Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols
    7.
    发明授权
    Accelerated process for preparing O-methyl phenols, N-methyl heteroaromatic compounds, and methylated aminophenols 有权
    制备O-甲基苯酚，N-甲基杂芳族化合物和甲基化氨基酚的加速方法

    公开(公告)号：US06596877B2

    公开(公告)日：2003-07-22

    申请号：US09982147

    申请日：2001-10-17

    申请人： Wen-Chung Shieh ,  Steven Dell

    发明人： Wen-Chung Shieh ,  Steven Dell

    IPC分类号： C07D23358

    CPC分类号： C07D235/06 ,  C07C41/16 ,  C07D209/08 ,  C07D209/86 ,  C07D235/18 ,  C07C43/2055 ,  C07C43/205

    摘要： An accelerated process for preparing an O-methyl phenol comprising reacting a phenol with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to another aspect, the invention provides an accelerated process for preparing an N-methyl heteroaromatic compound comprising reacting an NH-containing heteroaromatic compound with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. According to an additional aspect, the invention provides an accelerated process for preparing a methylated aminophenol comprising reacting an aminophenol having at least one N—H with dimethyl carbonate in the presence of a catalyst selected from 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-diazabicyclo[2.2.2]octane; and dimethylaminopyridine. The process of the invention is especially advantageous since the process: (1) utilizes an environmentally friendly methylating reagent, dimethylcarbonate; (2) produces a high yield of the O-methyl phenols, N-methyl aromatic amines, and/or methylated aminophenols, generally 97-100% conversion; and (3) does not require a high-pressure (autoclave) reactor.

    摘要翻译： 一种制备O-甲基苯酚的加速方法，包括使苯酚与碳酸二甲酯在选自1,8-二氮杂双环[5.4.0]十一碳-7-烯的催化剂存在下反应; 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 根据另一方面，本发明提供了一种制备N-甲基杂芳族化合物的加速方法，包括使含NH杂芳族化合物与碳酸二甲酯在选自1,8-二氮杂双环[5.4.0]十一碳烯 - 七烯 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 根据另一方面，本发明提供了一种制备甲基化氨基苯酚的加速方法，包括在选自1,8-二氮杂双环[5.4.0]十一碳-7-烯的催化剂存在下使具有至少一个NH的氨基苯酚与碳酸二甲酯反应 烯; 1,4-二氮杂双环[2.2.2]辛烷; 和二甲基氨基吡啶。 本发明的方法是特别有利的，因为该方法：（1）利用环境友好的甲基化试剂，碳酸二甲酯; （2）产生高产率的O-甲基苯酚，N-甲基芳族胺和/或甲基化氨基苯酚，一般为97-100％转化率; 和（3）不需要高压（高压釜）反应器。