Cesium carbonate → methyl 5-(1H-pyrazol-4-yl)thiophene-3-carboxylate

HRID 1914571노트

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HRID 1914571 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[S:7][CH:6]=1)=[O:4].C(OC([N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:21]2[CH:22]=[N:18][NH:19][CH:20]=2)[S:7][CH:6]=1)=[O:4]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 45873035Methyl 5-bromothiophene-3-carboxylate

생성물 1

HCID 58110358methyl 5-(1H-pyrazol-4-yl)thiophene-3-carboxylate

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
140 °C

실험 절차

5-Bromo-thiophene-3-carboxylic acid methyl ester (1.29 g, 5.84 mmol) was dissolved in DME (13.5 mL), IMS (4.5 mL) and water (2 mL) and), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.89 g, 6.43 mmol) and caesium carbonate (2.85 g, 8.77 mmol) were added followed by palladium tetrakis(triphenylphosphine) (0.675 g, 5.84 mmol). The reaction mixture was heated by microwave irradiation at 140° C. for 20 minutes and then diluted with water and extracted with DCM (×3). The organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on a silica II cartridge, eluting with 10 to 50% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give 5-(1H-pyrazol-4-yl)-thiophene-3-carboxylic acid methyl ester as a white, flocculent solid (0.728 g).

후처리

  1. extractionextracted with DCM (×3)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe residue was purified by chromatography on a silica II cartridge
  6. washeluting with 10 to 50% ethyl acetate in cyclohexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-8cf1a2a38ce746a5af269fc89293546d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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