Sodium Carbonate → 3-Bromo-5-(3-(trifluoromethyl)phenyl)pyridine

HRID 2117260Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CCO.O.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:10]([F:21])([F:20])[F:9])[CH:16]=2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3,5-dibromopyridine (1.2 g, 5 mmol), 3-trifluoromethylphenyl boronic acid (0.95 g, 5 mmol), tetrakis(triphenylphosphine)palladium (0) (0.23 g, 0.2 mmol), and sodium carbonate (1.1 g, 10 mmol) in EtOH (10 mL) and water (1 mL) were heated in an oil bath at 70° C. for 3 days. The mixture was cooled to RT and diluted with EtOAc (20 mL) and water (10 mL). The layers were partitioned and the organic layer was dried (Na2SO4), filtered and concentrated. Purification by chromatography (eluting with 10:1 hexanes/EtOAc) resulted in 0.4 g (26%) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 8.76 (d, 1H, J=2.1 Hz), 8.71 (d, 1H, J=2.1 Hz), 8.06 (dd, 1H, J=2.1, 2.1 Hz), 7.80 (s, 1H), 7.74-7.61 (m, 3H); APCI MS m/z 304.0, 302.0 (M+1).

Workup

temperatureThe mixture was cooled to RT
customThe layers were partitioned
dry with materialthe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customPurification
washby chromatography (eluting with 10:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-7af0c2c5a2ae4c9da13112cd06b5616c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442694B2

Reaction notes

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