Boron trifluoride → HCID 71008754, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[4-(2,2,2-Trifluoro-ethoxy)-phenyl]-octahydro-pyrrolo[3,4-c]pyridin-4-one (200 mg, 0.6 mmol), 1-iodo-2-methoxybenzene (300 mg, 1.3 mmol), Pd2(dba)3 (100 mg, 0.1 mmol), tBuOK (200 mg, 1.8 mmol) and 2-(Di-tert-butylphosphino)biphenyl (200 mg, 0.7 mmol) in toluene (20 mL) was refluxed overnight under nitrogen atmosphere. The mixture was cooled and filtrated, the resulting solution was concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to yield the intermediate ether (30 mg, 11%). This was taken up in anhydrous dichloromethane (20 mL). The mixture was cooled to −78° C., trifluoroborane (1 mL) was added drop-wise to the mixture and the mixture was stirred at −78° C. for 2 h, 1 h at room temperature and at reflux for 1 h. The mixture was poured into water (20 mL), extracted with dichloromethane (3×20 mL), the organic layers was combined, dried over anhydrous sodium sulphate, filtrated and concentrated. The residue was purified by silica gel column chromatography (eluting with ethyl acetate/petroleum ether=½) to yield the title compound (20 mg, 69%). 1H NMR (300 MHz, CDCl3): 7.29-7.13 (m, 4H), 7.10-6.86 (m, 5H), 4.38 (q, 2H, J=8.1 Hz), 3.79-3.26 (m, 6H), 3.08-2.92 (m, 2H), 2.27-1.92 (m, 2H). LC-MS: [M+1]+=407.2.

Provenance & Evidence