1,1'-Carbonyldiimidazole → HCID 71295693、化合物

HRID 1776822ノート

反応式

HRID 1776822 の反応式
[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

参加物

5

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 13163448HCID 13163448、化合物

生成物 1

HCID 71295693HCID 71295693、化合物収率 79.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e3f114d7f0994dbea2155128ca487bbe
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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