Water → HCID 18787048, compound

HRID 1107299Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.Br[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 85 °C

Procedure

4-(Trifluoromethoxy) phenyl boronic acid (1.3 g, 6.31 mmol) was dissolved in ethylene glycol dimethyl ether (50 ml). 3-Bromopyridine (1 ml, 9.5 mmol), aqueous sodium carbonate (2M, 30 ml), and Pd(dppb)Cl2 (100 mg) were added and the reaction mixture was stirred at 85° C. for 3 hours. The mixture was allowed to cool to room temperature, then water (200 ml) was added and the mixture was extracted with ethyl acetate (3×100 ml). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/ether (60:40) to give the title compound as an oil (1.26 g, 84%). 1H NMR (250 MHz, CDCl3) δ 8.84 (1H, s), 8.60 (1H, br d), 7.87 (1H, m), 7.61 (2H, m), and 7.36 (3H, m). m/z (ES+) 240 (M+1).

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with ethyl acetate (3×100 ml)
dry with materialThe combined organic fractions were dried (MgSO4)
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel
washeluting with hexane/ether (60:40)

Sources & evidence

ORD record: ord-7d06184c0a394224bb2b70dc6ca0a3de
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060469

Reaction notes

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