Synthesis of 2-bromo-6, 7-dihydrobenzo[6, 7] [l,4]oxazepino[4,5-a]indole

Synthesis of 2-bromo-6, 7-dihydrobenzo[6, 7] [l,4]oxazepino[4,5-a]indole

A solution of compound 2-(5-bromo-2-(2-bromoethoxy)phenyl)-lH-indole (1.97 g, 5 mmol) in 30 mL of DMF was cooled to 0 °C at N₂ atmosphere, NaH (600 mg, 15 mmol) was added at the same temperature. The reaction mixture was stirred at room temperature. After 8 hours, the reaction was quenched by water, extracted with EtOAc. The organic layer was washed with water and brine, dried over Na₂S0₄, filtered, and concentrated in vacuo.

Purification by flash chromatography on silica gel (petroleum ether : EtOAc = 50 : 1) provided 2-bromo-6,7-dihydrobenzo[6,7][l,4]oxazepino[4,5-a]indole as light yellow powder (0.8 g, 51%), which was also prepared from 4-bromo-2-(lH-indol-2-yl)phenol and 1,2-dibromoethane using similar method described in step 5 of Example 1. 

1H- MR (CDC1₃, 400 MHz) δ 7.96 (s, 1H), 7.66 (d, J= 7.6 Hz, 1H), 7.30-7.33 (m, 2H), 7.25-7.27 (m, 1H), 7.16 (t, J= 6.8 Hz, 1H), 6.95 (d, J= 8.8 Hz, 1H), 6.91 (s, 1H), 4.53-4.55 (m, 2H), 4.47-4.49 (m, 2H). 

MS (M+H)⁺: 314 / 316.

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