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

HRID 1036990Notes

Reaction equation

HRID 1036990 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-147c578313be43d0aa7d287197ebd703
Source dataset
uspto-grants-2013_10
Patent number
US08546438B2

Reaction notes

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