Water → 5-(2-methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid methyl ester

HRID 1914561

반응식

HRID 1914561 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[S:7][CH:6]=1)=[O:4].[CH3:11][N:12]1[C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.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:16]2[N:12]([CH3:11])[N:13]=[CH:14][CH:15]=2)[S:7][CH:6]=1)=[O:4]

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 45873035Methyl 5-bromothiophene-3-carboxylate

생성물 1

HCID 581103165-(2-methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid methyl ester수율 84.3%

시약·촉매·용매 2

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

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온도
140 °C

실험 절차

5-Bromo-thiophene-3-carboxylic acid methyl ester (0.193 g, 0.87 mmol) was combined with 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.2 g, 0.96 mmol), caesium carbonate (0.424 g, 1.3 mmol), and palladium tetrakis(triphenylphosphine) (0.1 g, 0.09 mmol) in DME (10 mL), IMS 2 mL) and water (1 mL). The reaction mixture was degassed then heated by microwave irradiation to 140° C. for 20 minutes. The mixture was diluted with water then extracted with DCM (×3) then the organic solution was dried over sodium sulfate, filtered and the solvent evaporated. The residue was purified by chromatography on a 5 g silica II cartridge, eluting with 5-30% ethyl acetate in cyclohexane to give 5-(2-methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid methyl ester as a brown oil (0.163 g). LCMS m/z 223.24 [M+H]+ R.T.=3.24 min (Analytical Method 6).

후처리

  1. customThe reaction mixture was degassed
  2. additionThe mixture was diluted with water
  3. extractionthen extracted with DCM (×3)
  4. dry with materialthe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by chromatography on a 5 g silica II cartridge
  8. washeluting with 5-30% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-8537e3153ad744b0b2bfd1d5ca84671d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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