Water → HCID 117988252, compound

HRID 2206264Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([F:21])([F:20])[CH2:9][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH:12]=1)(=O)=O.[OH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C(O)(=O)C>[CH2:13]([N:10]1[CH2:11][CH:12]=[C:7]([C:28]2[CH:29]=[CH:30][C:25]([OH:24])=[CH:26][CH:27]=2)[C:8]([F:21])([F:20])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1-benzyl-3,3-difluoro-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate (1.13 g), 4-hydroxyphenylboronic acid (0.43 g) and sodium carbonate (1.01 g) in DMF (10 mL) was added dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) (73 mg) under nitrogen atmosphere. The reaction mixture was stirred at 90° C. for 3 hr. The reaction mixture was added to water, and the mixture was adjusted to pH=5 with acetic acid, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (725 mg).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-6e4f552ab95f47059d42777d96d4091d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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