Sodium hydride → 2-(2-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropoxy)ethyl)isoindoline-1,3-dione

HRID 62200

反応式

HRID 62200 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[Br:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH2:32][CH:33]3[CH2:35][O:34]3)[C:23]3[C:28]([C:29]=2[CH:30]=1)=[CH:27][C:26]([Br:31])=[CH:25][CH:24]=3>C1COCC1.CCOC(C)=O>[Br:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([CH2:32][CH:33]([OH:34])[CH2:35][O:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=4)[C:7]3=[O:16])[C:23]3[C:28]([C:29]=2[CH:30]=1)=[CH:27][C:26]([Br:31])=[CH:25][CH:24]=3

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

生成物 1

HCID 580658792-(2-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropoxy)ethyl)isoindoline-1,3-dione収率 44%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium hydride dispersion (31.6 mg, 0.79 mmol) was added to a solution of N-(2-hydroxyethyl)-phthalimide (153.7 mg, 0.80 mmol) in anhydrous THF (1.2 ml, 0.67 M). The suspension is stirred for 15 minutes before the addition of carbazole epoxide 2-A. The reaction was stirred at room temperature for five minutes and then at 60° C. for 1 hour. The cooled reaction was diluted with EtOAc and washed with water. The aqueous layer was extracted and the combined organics were filtered over a celite pad. The Crude product was used without further purification. Yield=44%

後処理

  1. waitat 60° C. for 1 hour
  2. customThe cooled reaction
  3. washwashed with water
  4. extractionThe aqueous layer was extracted
  5. filtrationthe combined organics were filtered over a celite pad
  6. customThe Crude product was used without further purification

出典と根拠

ORDレコード
ord-f9d43b80ea2045f78aef1e1081c5222c
出典データセット
uspto-grants-2016_09
特許番号
US09446042B2

関連ノート

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