Nitrogen → HCID 71295692, compound

HRID 1776801Notes

Reaction equation

HRID 1776801 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][CH2:19]Br)=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:7]=1.N#N.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][CH2:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH:16]=[C:8]3[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 86728228HCID 86728228, compound

Product 1

HCID 71295692HCID 71295692, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 2-(5-bromo-2-(2-bromoethoxy)phenyl)-1H-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 Na2SO4, 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][1,4]oxazepino[4,5-a]indole as light yellow powder (0.8 g, 51%), which was also prepared from 4-bromo-2-(1H-indol-2-yl)phenol and 1,2-dibromoethane using similar method described in step 5 of Example 1. 1H-NMR (CDCl3, 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.

Workup

  1. additionwas added at the same temperature
  2. customthe reaction was quenched by water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (petroleum ether:EtOAc=50:1)

Sources & evidence

ORD record
ord-bb77d0af34d441e28a55788acf00eb24
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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