Methanol → 2-chloro-11-fluoro-6-(morpholinomethyl)-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indole

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Reaction Steps

To a solution of (2-chloro-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)(morpholino)methanone (60 mg, 0.16 mmol) in THF (2 mL) was added to BH3.SMe2 (1 mL, 1 mmol) at 0° C. After being stirred for overnight, MeOH and water was added, the mixture was extracted with EtOAc (10 mL*3). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=2:1) to provide 2-chloro-11-fluoro-6-(morpholinomethyl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole (50 mg, yield: 86.2%). 1H-NMR (CDCl3, 400 MHz) δ 7.28˜7.34 (m, 1H), 7.22˜7.26 (m, 1H), 7.13˜7.22 (m, 2H), 7.09 (d, J=8.4, 1H), 6.79˜6.86 (m, 1H), 6.43 (t, J=4.8 Hz, 1H), 3.45˜3.53 (m, 2H), 3.34˜3.43 (m, 2H), 2.80˜2.88 (m, 1H), 2.63˜2.70 (m, 1H), 2.30˜2.39 (m, 2H), 2.21˜2.29 (m, 2H). MS (M+H)+: 374.

Provenance & Evidence