Cesium carbonate → 1-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester

HRID 1748567ノート

反応式

HRID 1748567 の反応式
[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]([C:22]1[CH:23]=[CH:24][C:25](Br)=[N:26][CH:27]=1)(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([C:25]2[CH:24]=[CH:23][C:22]([C:19](=[O:21])[CH3:20])=[CH:27][N:26]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 11171190tert-butyl 1H-pyrrole-3-carboxylateHCID 156681955-Acetyl-2-bromopyridine

生成物 1

HCID 866925131-(5-Acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester収率 31.7%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A suspension of 1H-pyrrole-3-carboxylic acid tert-butyl ester (700 mg) described in Reference Example 50, 1,1′-bis(diphenylphosphino)ferrocene (35 mg), palladium acetate (9.4 mg), cesium carbonate (1.64 g) and 5-acetyl-2-bromopyridine (921 mg) in toluene (10 ml) was stirred at 100° C. for 8 hours. After completion of the reaction, the mixture was allowed to cool to room temperature, ice water was added thereto, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(5-acetylpyridin-2-yl)pyrrole-3-carboxylic acid tert-butyl ester (380 mg) as a white solid.

後処理

  1. customAfter completion of the reaction
  2. temperatureto cool to room temperature
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-d1ca1a8a6f3549d399ab335850cd181f
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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