S-ethyl 2-bromopyridine-4-carbothioate → 2-(2-Bromopyridine-4-carbonyl)-6-fluorobenzonitrile

To a degassed solution of S-ethyl 2-bromopyridine-4-carbothioate (5.0 g, 20.3 mmol) in anhydrous toluene (50 mL), Pd(OAc)2 (0.82 g, 3.66 mmol) was added followed by dropwise addition of 2-cyano-3-fluorophenylzinc iodide (0.5M in THF, 36.6 mL, 18.3 mmol). The reaction mixture was stirred at room temperature for 2 hours with continued bubbling of nitrogen. Water (50 mL) and saturated aqueous NH4Cl (100 mL) were added and the resulting mixture was extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography using a gradient of 25% to 100% ethyl acetate in hexanes to afford 3.4 g of the title compound (1.5 g, 27%).

1. customwith continued bubbling of nitrogen
2. additionWater (50 mL) and saturated aqueous NH4Cl (100 mL) were added
3. extractionthe resulting mixture was extracted with ethyl acetate (2×200 mL)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash column chromatography

ORD record

ord-f889585d78af4d4a81395297802d4fbb

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030500B2