Pyridine → HCID 89955707, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 10 (1.201 g, 12.00 mmol), 1F (3.3 g, 8.00 mmol), pyridine (1.937 ml, 24.00 mmol) in EtOAc (40.0 ml) was cooled down to −10° C. under Ar, T3P (50% wt in EtOAc) (9.52 ml, 16.00 mmol) was added dropwise and stirred at −10° C., then gradually warmed up to rt over night. The reaction mixture was washed with sat. aq. NaHCO3 twice, combined aqueous layer was back extracted with EtOAc. The combined EtOAc phases washed with brine, dried over MgSO4, filtered, concentrated. The crude product was then purified using silica gel chromatography to give 1G (4.06 g, 97%) as a white solid. 1H NMR (500 MHz, METHANOL-d4) δ 8.46 (d, J=5.0 Hz, 1H), 7.64 (s, 1H), 7.47 (dd, J=8.4, 2.1 Hz, 1H), 7.35 (s, 1H), 7.29 (d, J=8.3 Hz, 1H), 7.25 (m, 1H), 5.87-5.73 (m, 2H), 5.16-5.02 (m, 4H), 4.79-4.71 (m, 1H), 3.75 (s, 3H), 3.14-3.05 (m, 1H), 2.64-2.55 (m, 1H), 2.52-2.43 (m, 1H), 1.42 (s, 9H), 1.16 (d, J=6.9 Hz, 3H). MS (ESI) m/z: 495.1 (M+H)+.

Provenance & Evidence