Dimethylformamide → 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24]Br)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[CH2:26]([CH2:29][NH2:30])[CH:27]=C.[CH3:31]N(C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:30]([CH2:29][CH:26]=[CH2:27])[CH3:31])=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

参加物

反応物 3

HCID 6228Dimethylformamide

HCID 4437323-Buten-1-amine

HCID 695153545-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

生成物 1

HCID 695149675-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester収率 66%

実験手順

106 mg (0.25 mmol) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 2 ml DMF were treated with 71 mg (1 mmol) N-allylmethylamine at 50° C. for 2 h. The mixture was concentrated and purified by column chromatography on silica gel with CH2Cl2/MeOH 19:1 to give 68 mg (66%) 5-[4-(Allyl-methyl-amino)-butoxy]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as colorless solid, MS: 415 (MH+, 1Cl).