Ethyl Acetate → tert-Butyl 4-{[2-(trifluoromethyl)-6-vinylpyrimidin-4-yl]oxy}piperidine-1-carboxylate

HRID 1426353Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:3]=1.[C:26](OCC)(=O)[CH3:27]>CN(C=O)C.[F-].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:8]([F:11])([F:10])[C:6]1[N:5]=[C:4]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:3]=[C:2]([CH:26]=[CH2:27])[N:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of tert-butyl 4-{[6-chloro-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate (0.742 g, 1.94 mmol) in DMF (8.7 mL) was added (2-ethenyl)tri-n-butyltin (0.682 mL, 2.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (112 mg, 0.0972 mmol). The reaction solution was stirred at 65° C. overnight. The reaction solution was diluted with ethyl acetate and saturated KF solution. The aqueous layer was extracted with ethyl acetate three times. The combined organic solutions were dried over Na2SO4, filtered and concentrated. The residue was purified with silica gel column to give the desired product as light brown oil. LCMS (M+H)+: 374.2.

Workup

extractionThe aqueous layer was extracted with ethyl acetate three times
dry with materialThe combined organic solutions were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified with silica gel column

Sources & evidence

ORD record: ord-9ce962dae261406a9b526d335a466e24
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933085B2

Reaction notes

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