Potassium Carbonate → 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide

HRID 216323Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH3:9][O:10][N:11]([CH3:23])[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:12]([N:11]([O:10][CH3:9])[CH3:23])=[O:13])=[CH:15][CH:16]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Palladium tetrakis(triphenylphosphine) (1.38 g, 1.2 mmol) was added to a degassed, ambient temperature solution of 2-bromo-5-fluoropyridine (5 g, 28.4 mmol) and (4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (5 g, 23.9 mmol) and potassium carbonate (4.3 g, 31.1 mmol) in toluene/methanol (9.5:1) (105 mL). After stirring at 90° C. for 1.5 hr, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide.

Workup

concentrationthe reaction mixture was concentrated in vacuo
customThe residue was partitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0b6748ef8bb54121b161784cbe96fee9
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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