1,1'-Carbonyldiimidazole → HCID 71295693, 화합물

HRID 1776822노트

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HRID 1776822 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:15]=1>CN(C1C=CN=CC=1)C.ClCCl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[O:20][C:1](=[O:2])[N:22]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=4[CH:29]=[C:21]3[C:16]=2[CH:15]=1

참가 물질

5

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13163448HCID 13163448, 화합물

생성물 1

HCID 71295693HCID 71295693, 화합물수율 79.6%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

Carbonyldiimidazole (490 mg, 2 mmol) and DMAP (50 mg) were added to a solution of 4-bromo-2-(1H-indol-2-yl)phenol (576 mg, 2 mmol) in 20 mL of dichloromethane and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane/EtOAc 20:1) provided 2-bromo-6H-benzo[5,6][1,3]oxazino[3,4-a]indol-6-one as light yellow powder (500 mg, 79.6%). 1H-NMR (CDCl3, 400 MHz) δ 8.49 (d, J=8.4 Hz, 1H), 7.96 (s, 1H), 7.70 (d, J=7.2 Hz, 1H), 7.41˜7.53 (m, 3H), 7.22 (d, J=8.8 Hz, 1H), 7.07 (s, 1H). MS (M+H)+: 314/316.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (hexane/EtOAc 20:1)

출처 및 근거

ORD 기록
ord-e3f114d7f0994dbea2155128ca487bbe
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265773B2

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