1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-chloro-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-(4-chloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 3 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 yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 128 mg (86%) of a white solid. MS (ISP) 445.4 (M+H)+.

1. stirringAfter stirring for 3 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 yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1)

ORD record

ord-bf4a111da22b4f0fb9d44fcfc7b2d543

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2