Ethyl Acetate → HCID 86728244, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carbonitrile (500 mg, 1.77 mmol) in toluene (10 mL) was added DIBAL-H (505 mg, 3.55 mmol) in portion under nitrogen at −78° C. and then the mixture was stirred at −78° C. for 6 hours. The reaction mixture was quenched with ice water and extracted with EtOAc. Then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to provide the 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carbaldehyde (200 mg, yield: 40%) through the column chromatography (petroleum ether:EtOAc=5:1˜2:1). 1H-NMR (CDCl3, 400 MHz) δ 10.29 (s, 1H), 8.03 (s, 1H), 7.69 (dd, J1=0.8 Hz, J2=7.2 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.38 (d, J=8.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.05 (s, 2H). MS (M+H)+: 285/287.

Provenance & Evidence