Potassium Carbonate → Tert-butyl 4-(2-methyl-4-nitrophenoxy)pyridin-2-ylcarbamate

To a solution of tert-butyl 4-hydroxypyridin-2-ylcarbamate (4.12 g, 19.6 mmol) and 1-fluoro-2-methyl-4-nitrobenzene (3.34 g, 21.6 mmol) in DMF (40 mL) was added K2CO3 (4.06 g, 29.04 mmol). After heating to 65° C. for 64 hours, the mixture was cooled to room temperature and poured into ice water (200 mL). The reaction mixture was extracted several times with ethyl acetate. The combined organics were concentrated under reduced pressure. The residue was chromatographed (20% ethyl acetate in hexanes) to provide the product (2.03 g, 30%).

1. temperaturethe mixture was cooled to room temperature
2. extractionThe reaction mixture was extracted several times with ethyl acetate
3. concentrationThe combined organics were concentrated under reduced pressure
4. customThe residue was chromatographed (20% ethyl acetate in hexanes)

ORD record

ord-78620a617fd748c29ce9748025b19eeb

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648087B2