Nitrogen → HCID 71295692, 화합물

HRID 1776801노트

반응식

HRID 1776801 반응식
[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

참가 물질

5

반응물 3

HCID 947NitrogenHCID 24758Sodium hydrideHCID 86728228HCID 86728228, 화합물

생성물 1

HCID 71295692HCID 71295692, 화합물수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bb77d0af34d441e28a55788acf00eb24
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265773B2

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