5-Fluoroindole-2-carboxylic acid → HCID 22065999, compound

Participants

Reaction Steps

tert-Butyl 1,4-diazepane-1-carboxylate (2.0 g, 10 mmol, Aldrich), 5-fluoro-1H-indole-2-carboxylic acid (1.79 g, 10 mmol, Aldrich), and EDCI (1.92 g, 10 mmol) were combined in CH2Cl2 (30 mL) at room temperature and stirred for 24 hours. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CD3OD, 300 MHz) δ 1.46(s, 9H), 1.86–2.14(m, 2H), 3.40–3.58(m, 2H), 3.62–3.72(m, 2H), 3.75–4.05(m, 4H), 6.78(s, 1H), 6.99–7.09(m, 1H), 7.28–7.35(m, 2H); MS (DCI/NH3) m/z 362 (M+H)+.

Provenance & Evidence