Cesium carbonate → Ethyl 5-(3-chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylate

HRID 1036990ノート

反応式

HRID 1036990 の反応式
Br[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:13][C:9]1[CH:8]=[C:7]([C:6]2[S:5][C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][C:2]=2[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:19]#[N:20])[CH:26]=2)[CH:12]=[CH:11][CH:10]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58066739Ethyl 4-bromo-5-(3-chlorophenyl)thiophene-2-carboxylate

生成物 1

HCID 58066749Ethyl 5-(3-chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
50 °C

実験手順

Under argon, 3.20 g (9.26 mmol) of the compound from Example 10A are provided in 100 ml of 1,2-dimethoxyethane, and 1.36 g (9.26 mmol) of 3-cyanophenylboronic acid, 9.05 g (27.8 mmol) of cesium carbonate, 309 mg (0.65 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 62.4 mg (0.28 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. for three hours. The reaction mixture is subsequently diluted with water and extracted with dichloromethane, and the organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) on silica gel. 1.71 g (50% of theory) of the title compound are obtained.

後処理

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate gradient) on silica gel

出典と根拠

ORDレコード
ord-147c578313be43d0aa7d287197ebd703
出典データセット
uspto-grants-2013_10
特許番号
US08546438B2

反応ノート

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