Triethylamine → HCID 86686449, compound

Participants

Reaction Steps

To a stirred solution of 1-(pentan-2-yl)-1H-indol-5-ol (9) (2.60 g, 12.8 mmol) in dichloromethane (CH2Cl2, 40 mL) was added isopropyl isocyanate (10) (i-PrNCO, 1.63 g, 19.3 mmol), followed by triethylamine (NEt3, 0.90 mL). The solution was stirred at room temperature overnight, and then concentrated to dryness in vacuo. The resulting oil was purified by silica gel column chromatography (1:3 ethyl acetate/hexanes) to provide 1-(pentan-2-yl)-1H-indol-5-yl isopropylcarbamate (11) (3.6 g, 98%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.35 (d, J=2.0, 1H), 7.32 (d, J=9.0 Hz, 1H), 7.22 (d, J=3.0 Hz, 1H), 6.98 (dd, J=8.5, 2.0, 1H), 6.50 (d, J=3.0 Hz, 1H), 4.86 (d, J=6.5 Hz, 1H), 4.49 (m, 1H), 3.82 (m, 1H), 1.87 (m, 2H), 1.51 (d, J=6.5, 3H), 1.26 (m, 8H), 0.90 (t, J=7.5, 3H).

Provenance & Evidence