Methanol → 3,5-Dibromo-4-methoxypyridine

To a solution of MeOH (0.115 mL, 2.85 mmol) and THF (0.5 mL) at 0° C. was added sodium hydride (60% dispersion, 114 mg, 2.85 mmol). After stirring for 15 min, Intermediate 31B (600 mg, 1.900 mmol) was added, and the resulting mixture was stirred at room temperature for 19 hours, diluted with water (3 mL) and extracted with EtOAc (2×10 mL). The combined organics were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield Intermediate 31 (0.480 g, 1.798 mmol, 95% yield) as a beige color solid. MS (ES): m/z=267.9 [M+H]+. 1H NMR (400 MHz, MeOD) δ ppm 8.68 (2 H, s), 3.99 (3 H, s). Intermediate 31 was used in the synthesis of Example 185.

1. stirringthe resulting mixture was stirred at room temperature for 19 hours
2. extractionextracted with EtOAc (2×10 mL)
3. washThe combined organics were washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-fd661e44a93042c69357db454fa04fd8

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916553B2