Cesium carbonate → HCID 86728241, compound

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([C:16]=2[F:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]([OH:18])=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[Cs+].[Cs+].ClCI>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:16]([F:17])=[C:8]3[C:6]=2[N:7]=1

Participants

Procedure

A solution of 6-chloro-2-(3-fluoro-1H-indol-2-yl)pyridin-3-ol (120 mg, 0.46 mmol) and Cs2CO3 (452 mg, 1.39 mmol) in DMF (6 mL) was stirred at 100° C. (internal temperature), then chloroiodomethane (173 mg, 0.92 mmol) in DMF (1 mL) was added dropwise. After the reaction was completed according to TLC, the mixture was filtered and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=4:1) to provide 2-chloro-12-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (60 mg, yield: 47.6%). 1H-NMR (CDCl3, 400 MHz) δ 7.63 (d, J=8.0 Hz, 2H), 7.06˜7.28 (m, 4H), 5.76 (s, 2H). MS (M+H)+: 275/277.