6-Chloro-2-iodo-3-(trifluoromethyl)pyridine → (6-Chloro-3-(trifluoromethyl)pyridin-2-yl)(2-fluoropyridin-3-yl)methanone

To a solution of 6-chloro-2-iodo-3-(trifluoromethyl)pyridine (described in the literature: Eur. J. Org. Chem. 2004, 3793) (1.9 g, 6.180 mmol) in tetrahydrofuran (20 mL), cooled to −78° C., was added isopropyl magnesium chloride 2M in tetrahydrofuran (3.152 mL of 2 M, 6.304 mmol). The reaction mixture was stirred for 15 minutes. A solution of 2-fluoro-N-methoxy-N-methylnicotinamide (1.252 g, 6.798 mmol) in tetrahydrofuran (4 mL) was added and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was partitioned between a saturated solution of ammonium chloride and ethyl acetate. The organic extract was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a pale yellow oil (1.14 g, 61% yield).

1. stirringthe reaction mixture was stirred at −78° C. for 1 hour
2. customThe reaction mixture was partitioned between a saturated solution of ammonium chloride and ethyl acetate
3. extractionThe organic extract
4. washwas washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified on silica gel by flash column chromatography

ORD record

ord-e45b1099a5564c2bb0682060eac90451

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741931B2