1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,5-difluoro-phenyl)-ethyl]-amide

To a solution of 48 mg (0.3 mmol) of 1H-indole-7-carboxylic acid and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 91 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3,5-difluoro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 4 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 97 mg off-white solid (71%). MS (ISP) 447.3 (M+H)+.

1. stirringAfter stirring for 4 h at rt
2. extractionextracted with 2×50 ml EtOAc
3. washThe combined organic phases were washed with water and brine
4. dry with materialdried with magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6)

ORDレコード

ord-7e0325db4d20447a86b6aa9289dd91ff

出典データセット

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07259183B2