Indole → HCID 9909882, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in oil; 116 mg, 2.9 mmol) was added to a solution of indole (340 mg, 2.9 mmol) in NMP (2 ml) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then added dropwise to a cold (0° C.) solution of 2,4-dichloro-5-methylpyrimidine (489 mg, 3.0 mmol) in NMP (3 ml). The mixture was stirred at 0° C. for 3 hours and then 4-[3-(N,N-dimethyl)amino-2-hydroxypropoxy]aniline hydrochloride (Method 1, 500 mg, 1.76 mmol) was added. The mixture was heated at 100° C. overnight and then silica (2 g) was added. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluting with 0-5% 2.0M methanolic ammonia solution in DCM, to give the product as a white solid (166 mg, 13%). NMR: 2.1 (m, 9H), 2.3 (m, 2H), 3.9 (m, 3H), 4.8 (d, 1H), 6.85 (d, 1H), 6.9 (d, 2H), 7.2 (m, 2H), 7.6 (m, 5H), 8.5 (s, 1H), 9.5 (s, 1H); MS (MH+): 418.

Provenance & Evidence