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

HRID 626043Notes

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-19e3a439a6da4b60b9b3e5578199598d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309179B2

Reaction notes

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