Nitrogen → HCID 71295692、化合物

HRID 1776801ノート

反応式

HRID 1776801 の反応式
[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

参加物

5

反応物 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 86728228HCID 86728228、化合物

生成物 1

HCID 71295692HCID 71295692、化合物収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bb77d0af34d441e28a55788acf00eb24
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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