Cesium carbonate → HCID 86728231, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 6-chloro-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-3-ol (200 mg, 0.727 mmol) and Cs2CO3 (472 mg, 1.45 mmol) in DMF (15 mL) was added chloroiodomethane (192 mg, 1.09 mmol) in DMF (2 mL) dropwise at 100° C. under N2. The mixture was stirred at 100° C. for 1 hour. The mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine and dried over Na2SO4. After concentrated, the resulting residue was purified using Pre-TLC to provide 2-chloro-10-methoxy-6H-pyrido[2,3-e]pyrido[2′,3′:4,5]pyrrolo[1,2-c][1,3]oxazine (110 mg, yield: 52%). 1H-NMR (CDCl3, 400 MHz) 7.44 (d, J=8.8 Hz, 1H), 7.26 (d, J=8.8 Hz, 1H), 7.16 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 5.81 (s, 2H), 3.95 (s, 3H). MS (M+H)+: 288/290.

Provenance & Evidence