Sodium Carbonate → 2-Butoxy-3-(2-fluoro-5-trifluoromethyl-phenyl)-5-methyl-pyridine

HRID 1766443Notes

Reaction equation

Br[C:2]1[C:3]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:10]([O:9][C:3]1[C:2]([C:16]2[CH:17]=[C:18]([C:21]([F:23])([F:24])[F:22])[CH:19]=[CH:20][C:15]=2[F:14])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=1)[CH2:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: 90 °C

Procedure

3-Bromo-2-butoxy-5-methyl-pyridine (0.96 g, 3.9 mmol) was dissolved in toluene (6 mL). To this solution was added [2-fluoro-5-(trifluoromethyl)phenyl]-boronic acid (1.2 g, 5.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloro-methane complex (161 mg), and 2 N sodium carbonate solution (5.9 mL). The whole mixture was heated with stirring at 90° C. for 18 h, cooled to room temperature and eluted with ethyl acetate over 10 g ChemElut (Varian). The solvent was evaporated and the residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient) to yield 0.99 g of the title compound as a yellow oil, MS (ISP) 328.3 (M+H)+.

Workup

temperatureThe whole mixture was heated
temperaturecooled to room temperature
washeluted with ethyl acetate over 10 g ChemElut (Varian)
customThe solvent was evaporated
customthe residue was purified by column chromatography on silica (n-heptane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-00bc017682f7447cba32cff5fe8e74e2
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229999B2

Reaction notes

Loading…