Ammonia → HCID 54767999, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-3-[6-(4-phenoxyphenyl)-1H-indol-3-yl]propionamide (15) was prepared as follows: A mixture of compound 14 prepared in Example 4 (0.2 g) and NH3 (7N in MeOH, 6 mL, and 28% aqueous, 2 mL) was shaken at 70° C. for 16 hours. EtOAc (40 mL) and water (10 mL) were added to the reaction mixture. The organic layer was separated, concentrated and purified by column (EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.5) to afford compound 15 as a brown solid (0.1 g, 53%): 1H-NMR (400 MHz, CD3OD) δ: 7.6 (d, 1H, 8.3 Hz), 7.46-7.55 (m, 3H), 7.18-7.28 (m, 3H), 7.06 (s, 1H), 6.92-7.05 (m, 5H), 3.58-3.62 (m, 1H), 3.1-3.15 (m, 1H), 2.88-2.94 (m, 1H); LC/MS: m/z=372.1 [M+H]+ (Calc: 371.4).

Provenance & Evidence