Pyridine → HCID 66793945, compound

Participants

Reaction Conditions

Reaction Steps

To 5-pyridin-3-yl-1,3-dihydro-indol-2-one (CAS#220904-98-3, 63 mg, 0.3 mmol) was added freshly prepared tricyclopropyl-bismuthine [(J. Am. Chem. Soc., 2007, 129, 44-45), CAS#925430-09-7, 250 mg, 0.75 mmol], Cu(OAc)2 (82 mg, 0.45 mmol) and dichloromethane (3 ml). The reaction mixture was degassed by sparging with argon for 5 min. Then pyridine (0.073 ml, 0.9 mmol) was added and the reaction was heated at 75° C. for 1.5 hr. The reaction mixture was cooled to room temperature and then directly loaded on to a silica gel flash chromatography column. The 1-cyclopropyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one was eluted via a gradient of ethyl acetate-heptane (0 to 100%); HRMS: (ESI) m/z 251.1173 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.88-1.01 (m, 2H), 1.07-1.19 (m, 2H), 2.60-2.76 (m, 1H), 3.60 (s, 2H), 7.22-7.31 (m, 1H), 7.49 (s, 1H), 7.55 (d. J=8.5 Hz, 1H), 7.81 (br. s., 1H), 8.36 (d, J=7.7 Hz, 1H), 8.63 (br. s., 1H), 8.92 (br. s., 1H.

Provenance & Evidence