反応式
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH:21]=[CH:22][NH:23]3)=[CH:19][CH:18]=2)=[O:16])=[CH:10][C:9]=1[Cl:26].[OH-].[NH4+]>C(O)(=O)C.O.ClCCl>[CH3:5][O:6][C:7](=[O:27])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH:25]=[C:24]3[C:20]([CH2:21][CH2:22][NH:23]3)=[CH:19][CH:18]=2)=[O:16])=[CH:10][C:9]=1[Cl:26]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 0 °C
実験手順
Sodium cyanoborohydride (2.6 g, 41.6 mmol, 3 equiv.) was added to a stirred solution of 2-chloro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester (1.4 g, 4.2 mmol, 1 equiv.) in acetic acid (25 mL) over 5 minutes at room temperature. The mixture was stirred for 30 minutes then cooled to 0° C. and poured onto concentrated ammonium hydroxide (78 mL, d=0.880) at 0° C. The mixture was diluted with water (25 mL) and dichloromethane (25 mL), the organic layer was separated and the aqueous layer extracted with dichloromethane (2×25 mL). The combined organic layers were dried over Na2SO4 and the solvent removed under vacuum to afford crude 2-chloro-4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester, 0.75 g, this material was taken onto the next step without further purification. LC @215 nm; Rt 1.04: 71%, m/z (ES+): 331 (M+H+.).
後処理
- customthe organic layer was separated
- extractionthe aqueous layer extracted with dichloromethane (2×25 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- customthe solvent removed under vacuum
出典と根拠
- ORDレコード
- ord-3677983030114d40a78d540af3723026
- 出典データセット
- uspto-grants-2010_05
- 特許番号
- US07713996B2
関連ノート
読み込み中…