Dimethylamine → HCID 22638775, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[2-(2-oxo-ethyl)-cyclopropyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (50 mg, 0.13 mmol), dimethylamine (0.2 ml of a 2M solution in THF, 0.4 mmol), and 112 mg (0.53 mmol) sodium triacetoxyborohydride in ethyl alcohol (2 ml), was stirred for 12 hr at 70° C. Sodium hydroxide (15 equivalents of a 1N solution) was added and the mixture was stirred for 45 min at 75° C. The reaction mixture was cooled, diluted with water (3 ml), and extracted twice with ethyl acetate (10 ml). The ethyl acetate extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to give 3-[2-(2-diethylaminoethyl)-cyclopropyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (8.2 mg, 22%). MS m/e 282.22 (MH+).

Provenance & Evidence