Cesium carbonate → Ethyl 4-bromo-5-(3-cyanophenyl)furan-2-carboxylate

HRID 2190115Notes

Reaction equation

HRID 2190115 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:5][C:6]=1Br.[C:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)#[N:14].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.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[O:5][C:6]=1[C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([C:13]#[N:14])[CH:20]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27343253-Cyanophenylboronic acid2×HCID 5161728Ethyl 4,5-dibromofuran-2-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 58064801Ethyl 4-bromo-5-(3-cyanophenyl)furan-2-carboxylate

Reagents, catalysts & solvents 2

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

Procedure

Under argon, 3.00 g (10.1 mmol) of the compound from Example 2A are provided in 96 ml of 1,2-dimethoxyethane, and 1.63 g (11.1 mmol) of 3-cyanophenylboronic acid, 9.84 g (30.2 mmol) of cesium carbonate, 0.14 g (0.30 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 0.16 g (0.71 mmol) of palladium(II) acetate are added. The mixture is stirred at RT overnight. 0.44 g (3.02 mmol) of 3-cyanophenylboronic acid are subsequently added, and the mixture is stirred at RT for a further 24 h. The mixture is concentrated and the crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1). 1.15 g (36% of theory) of the title compound are obtained.

Workup

  1. stirringthe mixture is stirred at RT for a further 24 h
  2. concentrationThe mixture is concentrated
  3. customthe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-086503b2deb345b3851241edacb4b5eb
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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