Реакция #60683

ord-414dd79b9a714847a5118d94743e4ad9

Уравнение реакции

CC(C)(C)OC(=O)N1CCC(COCC(N)c2ccccc2F)CC1
4-[2-amino-2-(2-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester
O=C(O)c1ccc2cc[nH]c2c1
indole-6-carboxylic acid
→
CC(C)(C)OC(=O)N1CCC(COCC(NC(=O)c2ccc3cc[nH]c3c2)c2ccccc2F)CC1
4-{2-[(1H-Indole-6-carbonyl)amino]-2-(2-fluorophenyl)ethoxy-methyl}piperidine-1-carboxylic acid tert-butyl ester

Реактанты

CC(C)(C)OC(=O)N1CCC(COCC(N)c2ccccc2F)CC1
4-[2-amino-2-(2-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester
O=C(O)c1ccc2cc[nH]c2c1
indole-6-carboxylic acid

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеafforded
  2. 2
    Другоеafter purification (SiO2: 0 to 40% 2 N ammonia/methanol solution in DCM), 355 mg (53%) of the title compound

Методика

Using coupling method A, 4-[2-amino-2-(2-fluorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (480 mg, 1.4 mmol) and indole-6-carboxylic acid (242 mg, 1.5 mmol) afforded, after purification (SiO2: 0 to 40% 2 N ammonia/methanol solution in DCM), 355 mg (53%) of the title compound.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07427632B2uspto-grants-2008_09