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

HRID 1748567노트

반응식

HRID 1748567 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d1ca1a8a6f3549d399ab335850cd181f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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