Water → HCID 67975659, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-bromo-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate F9 (1.5 g, 4.25 mmol) in DMF (30 mL) was added Pd(PPh3)4 (751 mg, 0.63 mmol) and Zn(CN)2 (1.00 g, 8.51 mmol). The solution was stirred at 100° C. for 16 h. After cooling, water was added and the solution was extracted with ethyl acetate. The organic layer was washed with brine three times, dried and concentrated. The crude material was dissolved in 50 ml acetonitrile in which were added Boc2O (5.5 g, 25.2 mmol), NEt3 (6 ml), and DMAP (520 mg, 4.26 mmol). The resulting mixture was stirred for 16 h. The dark brown solution was concentrated under vacuum, and the residue was dissolved in ethyl acetate. The organic layer was washed twice with HCl (1N), brine, dried and concentrated under vacuum. The residue was purified by flash chromatography eluting with ethyl acetate and cyclohexane (10/90 to 30/70 over 30 min.) to give 880 mg of the desired compound F11 as a beige gum (69%). LCMS (method E): 0.87 min; ES+: 619 [2M+Na].

Provenance & Evidence