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

HRID 1036990노트

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HRID 1036990 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-147c578313be43d0aa7d287197ebd703
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546438B2

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