Cesium carbonate → 5-bromo-3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

A mixture of Example 182A (367 mg, 0.965 mmol), 2,4-difluorophenol (111 μl, 1.158 mmol) and cesium carbonate (472 mg, 1.448 mmol) in 8 mL DMSO was heated under nitrogen at 90° C. for 1.5 hours. The mixture was partitioned between water and ethyl acetate (80 mL). The aqueous phase was extracted with ethyl acetate (2×60 mL). The combined organics were washed with water (2×), saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel with a gradient of 10-70% ethyl acetate in heptanes to give the title compound (331 mg, 0.742 mmol, 77% yield) as a yellow solid.

1. customThe mixture was partitioned between water and ethyl acetate (80 mL)
2. extractionThe aqueous phase was extracted with ethyl acetate (2×60 mL)
3. washThe combined organics were washed with water (2×), saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated
7. customthe residue was purified by column chromatography on silica gel with a gradient of 10-70% ethyl acetate in heptanes

ORD record

ord-afd6f75300f544318d5325cf04d77f86

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321764B2