tert-Butanol → HCID 22668308, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(tert-butoxycarbonyl)-2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-5-carboxylic acid (6-1, 0.200 mg, 0.49 mmol, 1 equiv), diphenylphosphoryl azide (128 μL, 0.59 mmol, 1.2 equiv), and triethylamine (89 μL, 0.64 mmol, 1.3 equiv) in t-BuOH (30 mL) was heated at 100° C. for 2 hours. Cuprous chloride (4.9 mg, 0.05 mmol, 0.1 equiv) was added and the resulting mixture was heated at 100° C. for 24 hours. The solution was concentrated, and the residue was partitioned between and saturated aqueous NaHCO3 solution (75 mL) and EtOAc (3×60 mL). The combined organic layers were washed once with water (150 mL) then brine (150 mL) and dried over sodium sulfate and concentrated. The residue was purified by reverse-phase liquid chromatography (H2O/CH3CN gradient with 0.1% TFA present) to provide tert-butyl 5-[(tert-butoxycarbonyl)amino]-2-(2-oxo-1,2-dihydro-3-quinolinyl)-1H-indole-1-carboxylate (9-1). 1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.37 (bs, 1H), 8.05 (s, 1H), 7.92 (d, 1H, J=7.8 Hz), 7.82 (s, 1H), 7.52 (m, 2H), 7.35 (m, 2H), 7.21 (m, 2H), 6.72 (s, 1H), 1.50 (s, 9H), 1.34 (s, 9H).

Provenance & Evidence