Dichloromethane → 2-Fluoro-6-(5-fluoro-2-methoxy-4-vinylphenoxy)pyridine

HRID 1023953Notes

Reaction equation

Br[C:2]1[C:15]([F:16])=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=2)=[C:4]([O:17][CH3:18])[CH:3]=1.ClCCl.C(=O)([O-])[O-].[K+].[K+].[CH:28](B1OC(C)(C)C(C)(C)O1)=[CH2:29]>O.C(#N)C>[F:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:14]=[C:15]([F:16])[C:2]([CH:28]=[CH2:29])=[CH:3][C:4]=2[O:17][CH3:18])[N:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To 2-(4-bromo-5-fluoro-2-methoxyphenoxy)-6-fluoropyridine (227 mg, 0.71 mmol) were added [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (58.9 mg, 0.07 mmol) and potassium carbonate (597 mg, 4.26 mmol). To the mixture were added acetonitrile (4 mL), water (1.3 mL) and vinyl boronic acid pinacol ester (180 μL, 1.07 mmol). The reaction was flushed with argon, and left to stir for 3 days at 60° C. The reaction mixture was then filtered on celite, rinsed with dichloromethane and concentrated. After purification by preparative TLC (cyclohexane/ethyl acetate: 70/30), the title product was isolated as an orange oil (166 mg, 89%).

Workup

customThe reaction was flushed with argon
waitleft
filtrationThe reaction mixture was then filtered on celite
washrinsed with dichloromethane
concentrationconcentrated
customAfter purification by preparative TLC (cyclohexane/ethyl acetate: 70/30)

Sources & evidence

ORD record: ord-4813e6a6494d42f6a04d8cfda6e870fa
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

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