p-Toluenesulfonic acid → HCID 71295526, compound

Participants

Reaction Conditions

Reaction Steps

Cyclopropanecarbaldehyde (70 mg, 1.0 mmol) and PTSA (17 mg, 0.1 mmol) were added to a solution of 4-bromo-2-(3-chloro-1H-indol-2-yl)phenol (110 mg, 0.34 mmol) in toluene (2 mL). The mixture was allowed to stir at 110° C. for about 15 hours. The reaction solution was extracted by EtOAc, and the combined organic layers were washed with H2O (3×10 mL), brine and dried over Na2SO4. The solvent was removed and the crude product was Purified using prep-TLC to provide the desired product of 2-bromo-12-chloro-6-cyclopropyl-6H-benzo[5,6][1,3]oxazino[3,4-a]indole (40 mg, yield: 31.3%). 1H-NMR (CDCl3, 400 MHz) δ 8.42 (m, 1H), 7.63 (t, J=0.4 Hz, 1H), 7.30˜7.35 (m, 2H), 7.15˜7.24 (m, 2H), 6.93 (m, 1H), 5.62 (d, J=0.8 Hz, 1H), 1.36˜1.45 (m, 1H), 0.50˜0.56 (m, 4H). MS (M+H)+: 374/376.

Provenance & Evidence