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

HRID 2190117Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=1.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[C:25]([F:27])[CH:26]=1.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>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:3]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:5][C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[CH:8]=2)[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under argon, 1.45 g (4.53 mmol) of the compound from Example 8A are provided in 50 ml of 1,2-dimethoxyethane, and 0.79 g (4.53 mmol) of 3-chloro-5-fluorophenylboronic acid, 4.43 g (13.6 mmol) of cesium carbonate, 0.15 g (0.32 mmol) of dicyclohexyl[2′,4′,6′-tri(propan-2-yl)biphenyl-2-yl]phosphane and 0.03 g (0.14 mmol) of palladium(II) acetate are added. The mixture is stirred at 50° C. overnight. The mixture is concentrated and the crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1). 1.05 g (43% of theory) of the title compound with a purity of 68% are obtained.

Workup

concentrationThe mixture is concentrated
customthe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record: ord-421aa5f8d1614a958059177163b5bcb2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324268B2

Reaction notes

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