Cesium carbonate → HCID 68414099, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2,5-dibromopyridin-3-yl)-N-methylmethanamine (95 mg, 0.47 mmol), azetidinone (34 mg, 0.47 mmol), Cs2CO3 (308 mg, 0.94 mmol) in 5 mL of toluene was degassed with bubbling argon for 30 min followed by the addition of Pd2(dba)3 (6 mg, 0.01 mmol) and Xantphos (12 mg, 0.02 mmol). The resulting yellow solution was then stirred at 90° C. 18 h. The dark coloured solution was removed from the heat and poured over a pad of celite washing with 50 mL of ethyl acetate. The filtrate was diluted with 50 mL of water, the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified using flash chromatography on silica gel using 95% dichloromethane:methanol to obtain the product as a orange sticky solid. Yield 66 mg (73%); 1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, J=4.8 Hz, 1H), 7.28 (d, J=7.2 Hz, 1H), 6.78 (m, 1H), 4.92 (bs, 1H), 4.51 (s, 2H), 3.58 (q, J=6.0 Hz, 2H), 3.04 (t, J=6.8 Hz, 2H), 2.84 (s, 3H); ESI MS m/z 192 [C10H13N3O+H]+

Provenance & Evidence