N-bromobutanimide → 4-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

HRID 642353ノート

反応式

HRID 642353 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[S:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([Br:22])[C:9]2[S:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:14][C:8]=2[C:7]=1[OH:21])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 684268667-Hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester

生成物 1

HCID 866173574-Bromo-7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester収率 71.1%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 7-hydroxy-2-phenyl-thiazolo[5,4-c]pyridine-6-carboxylic acid ethyl ester (2.10 g, 7.01 mmole), N-bromosuccinimide (1.31 g, 7.36 mmole) and benzoyl peroxide (84.9 mg, 0.35 mmole) in carbon tetrachloride (40 ml) was refluxed for 2 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (1.89 g). MS: (+) m/z 379.18, 381.18 (M+1, 79Br/81Br).

後処理

  1. temperaturewas refluxed for 2 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

出典と根拠

ORDレコード
ord-3663eb51409d4d75b56112ff17353f86
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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