Water → N-{5-[3-(trifluoromethyl)phenyl]pyridin-3-yl]benzamide

HRID 876244Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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.CN(C=O)C>[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[C:4]([NH:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH:5]=[N:6][CH:7]=2)[CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 85 °C

Procedure

At 50° C., 1.95 g (7.02 mmol) of N-(5-bromopyridin-3-yl)benzamide, 2.00 g (10.5 mmol) of [3-(trifluoromethyl)phenyl]boronic acid and 1.49 g (14.04 mmol) of sodium carbonate were dissolved in 12 ml of 1,2-dimethoxyethane, 3.5 ml of water and 261 ml of DMF. The mixture was flushed with argon, 41 mg (0.04 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 85° C. for 12 h. The reaction mixture was concentrated slightly on a rotary evaporator, diluted with water and extracted with dichloromethane. The organic phase was concentrated under reduced pressure and the residue was purified by column chromatography (cyclohexane/ethyl acetate 2:1). Yield: 860 mg (35% of theory)

Workup

additionwere added
concentrationThe reaction mixture was concentrated slightly on a rotary evaporator
additiondiluted with water
extractionextracted with dichloromethane
concentrationThe organic phase was concentrated under reduced pressure
customthe residue was purified by column chromatography (cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record: ord-79bd6e187b09412ab402d4c32c18bc20
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987248B2

Reaction notes

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