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Thursday, 2 June 2016

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

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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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