Triethylamine → HCID 86686449, compound

Participants

Reaction Steps

To a stirred solution of 1-(pentan-2-yl)-1H-indol-5-ol (9) in CH2Cl2 (180 mL) was added i-PrNCO (5.37 mL, 54.6 mmol, 1.5 equiv.) and NEt3 (1.52 mL, 10.9 mmol, 0.30 equiv.), respectively. The reaction mixture was stirred at room temperature for 21 h, then concentrated to dryness in vacuo affording a dark, viscous liquid. The crude product was purified by flash column chromatography (2:1 hexanes/ethyl acetate) to give a beige solid, which was further purified by recrystallization from 100 mL of hexanes. Analytically pure product (11) was obtained as a white solid (6.29 g, 55% three-step yield). 1H NMR (500 MHz, CDCl3) δ7.33 (d, J=2.1 Hz, 1H), 7.31 (d, J=8.9 Hz, 1H), 7.19 (dd, J=8.8, 2.2 Hz, 1H), 6.47 (d, J=3.1 Hz, 1H), 4.83 (d, J=6.6 Hz, 1H), 4.45 (m, 1H), 3.91 (m, 1H), 1.87 (m, 1H), 1.76 (m, 1H), 1.48 (d, J=6.8 Hz, 3H), 1.30-1.13 (m, 8H), 0.87 (t, J=7.4 Hz, 3H).

Provenance & Evidence