4-Fluorophenylboronic acid → HCID 18444638, compound

HRID 1786612Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][O:20][C:19]=2[CH3:23])=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:22]=[CH:21][O:20][C:19]=3[CH3:23])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of (4-fluoro-phenyl)-boronic acid (300 mg, 2.1 mmoles), 3-(4-iodophenoxymethyl)-2-methyl-furan (123) (500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed, treated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg) and the mixture was agitated at 95° C. for 12 hours under an argon atmosphere. The mixture was concentrated in vacuo, partitioned between water (100 ml) and diethyl ether (200 ml). The aqueous phase was re-extracted with diethyl ether, and the combined etheral phases were dried and evaporated. The residue was purified by flash chromatography, using diethyl ether as eluent, to afford compound 124 (200 mg) as a solid. This material was used directly.

Workup

customwas degassed
additiontreated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg)
concentrationThe mixture was concentrated in vacuo
custompartitioned between water (100 ml) and diethyl ether (200 ml)
extractionThe aqueous phase was re-extracted with diethyl ether
customthe combined etheral phases were dried
customevaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-30912a3d6da24e659691cf8a35221043
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507754B2

Reaction notes

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