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

Temperature

0 °C

To a solution of the title compound of step 1 (500 mg, 2.3 mmol) stirred at 0° C. in DMF (5 mL) was added NaH (68 mg, 2.81 mmol, 60% in mineral oil). After stirring at 0° C. for 30 min, methyl iodide (400 mg, 2.8 mmol) was added dropwise. The ice bath was removed, and mixture was stirred at rt for 4 h. The reaction mixture was treated with saturated NH4Cl (aq. 30 mL) and extracted with EtOAc (30 mL×2). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (PE/EtOAc=10:1) to give the title compound (500 mg, 94%). 1H NMR (CDCl3, 400 MHz) δ 7.78 (d, J=2.0 Hz, 1H), 7.30 (s, 1H), 6.70 (d, J=2.0 Hz, 1H), 3.66 (s, 3H). LCMS (M+H)+=229.

1. customThe ice bath was removed
2. stirringmixture was stirred at rt for 4 h
3. additionThe reaction mixture was treated with saturated NH4Cl (aq. 30 mL)
4. extractionextracted with EtOAc (30 mL×2)
5. washThe combined organic layers were washed with brine (30 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by chromatography on silica gel (PE/EtOAc=10:1)

ORD record

ord-0520318f8f684766a1c394512756af2d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115114B2