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

HRID 2068615
ノート
印刷プレビュー

反応式

HRID 2068615 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water
溶媒
2 回
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e47e8a429be40ea84540859e6cf2085
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299063B2

反応ノート

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