Methyl iodide → 4-Bromo-2-chloro-6-methylfuro[2,3-c]pyridin-7-one

A 0.2 M solution of 4-bromo-2-chlorofuro[2,3-c]pyridin-7-ol (143 mg, 0.6 mmol) and K2CO3 (200 mg, 1.45 mmol) in DMF stirred at 0° C. under an atmosphere of nitrogen was treated with MeI (99 mg, 0.7 mmol). The ice bath was removed; the mixture was stirred at rt overnight. The reaction mixture was treated water (15 mL) and was extracted with EtOAc (3×10 mL). The combined organic layers were washed with water (15 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel using a gradient of EtOAc (10 to 100%) in hexanes to afford the title compound (113 mg, 85%) as a white solid. LCMS (M+H)+=263.

1. customThe ice bath was removed
2. additionThe reaction mixture was treated water (15 mL)
3. extractionwas extracted with EtOAc (3×10 mL)
4. washThe combined organic layers were washed with water (15 mL), brine (20 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by chromatography on silica gel using a gradient of EtOAc (10 to 100%) in hexanes

ORD record

ord-d5c553b453014477932c5c014edfa7a2

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034900B2