Water → (2-chloro-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-6-yl) methanol

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Reaction Steps

To a solution of ethyl 2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-6-carboxylate (3 g, 8.73 mmol) and NaBH4 (1.58 g, 43.67 mmol) in CH3OH/dichloromethane (30 mL/10 mL) was stirred at room temperature for 2 hours. The mixture was poured to H2O and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to provide (2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methanol (2.54 g, yield: 95.5%). 1H-NMR (DMSO-d6, 400 MHz) δ 7.60 (d, J=8.8 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.22˜7.28 (m, 1H), 7.08 (s, 1H), 6.94 (dd, J=10.4, 8.4 Hz, 1H), 6.78 (t, J=4.0 Hz, 1H), 5.29 (t, J=6.0 Hz, 1H), 3.71˜3.78 (m, 1H), 3.61˜3.67 (m, 1H). MS (M+H)+: 305.

Provenance & Evidence