Butyl bromide → HCID 46221940, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared according to general procedure E described in Scheme 2. 2-(1-Isopropyl-1H-indol-3-yl)-2-oxo-N-(piperidin-4-yl)acetamide hydrochloride (200 mg, 0.64 mmol) was treated with acetonitrile (3 mL), K2CO3 (265 mg, 1.91 mmol), and n-butyl bromide (175 mg, 1.28 mmol). The reaction mixture was stirred at 65° C. for 72 h and was then concentrated under reduced pressure. The crude material was purified on silica gel (Biotage, 2-10% MeOH/DCM, 30 min.) to provide the title compound as a pink solid (68 mg, 29% yield): 1H NMR (400 MHz, CDCl3): δ 9.11 (s, 1H), 8.43 (t, 1H), 7.56 (d, 1H), 7.43 (q, 1H), 7.35 (t, 2H), 4.71 (m, 1H), 3.90 (m, 1H), 3.03 (d, 2H), 2.48 (d, 2H), 2.31 (t, 2H), 2.05 (d, 2H), 1.80 (m, 2H), 1.61 (d+m, 8H), 1.34 (m, 2H), 0.94 (t, 3H);

Provenance & Evidence