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Diethyl Ether → 5-Pyridin-4-yl-thiophene-3-carboxylic acid ethyl ester

HRID 2068615
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HRID 2068615 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9](Br)[S:8][CH:7]=1)=[O:5])[CH3:2].[N:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOCC>O.COCCOC>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:15]2[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=2)[S:8][CH:7]=1)=[O:5])[CH3:2]
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참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

생성물 1

HCID 581102865-Pyridin-4-yl-thiophene-3-carboxylic acid ethyl ester수율 2.9%

시약·촉매·용매 2

HCID 962Water
용매
2회
HCID 80711,2-Dimethoxyethane용매

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온도
140 °C

실험 절차

5-Bromo-thiophene-3-carboxylic acid ethyl ester (5.26 mmol), 4-pyridylboronic acid (5.26 mmol), caesium carbonate (7.9 mmol) and palladium (0) tetrakis-triphenylphosphine (0.53 mmol) were dissolved in a mixture of water (10 mL), IMS (20 mL) and DME (50 mL). The reaction mixture was heated by microwave irradiation to 140° C. for 10 minutes, and then ether (100 mL) and water (20 mL) were added. The organic solution was washed with water, dried with anhydrous magnesium sulfate, filtered and the solvent evaporated to give brown oil. The residue was purified by flash chromatography on silica. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.035 g) as an off-white solid. LCMS m/z 234.04 [M+H]+ R.T.=2.10 min. (Analytical Method 5).

후처리

  1. washThe organic solution was washed with water
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customto give brown oil
  6. customThe residue was purified by flash chromatography on silica
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-1e47e8a429be40ea84540859e6cf2085
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299063B2

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