Methyl iodide → Methyl 4-bromo-6-methyl-7-oxo-6,7-dihydrothieno[2,3-c]pyridine-2-carboxylate

Temperature

0 °C

To a solution of methyl 4-bromo-7-hydroxythieno[2,3-c]pyridine-2-carboxylate (300 mg, 1.04 mmol) stirred at 0° C. in DMF (6.6 mL) under an atmosphere of nitrogen was added K2CO3 (358 mg, 2.6 mmol). After stirring at 0° C. for 15 min, methyl iodide (177 mg, 1.3 mmol) was added dropwise. The ice bath was removed, and mixture was stirred at rt for 20 min, 50° C. for 2 h, and rt for 10 h. The reaction mixture was treated with water (8 mL) and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography using a gradient of EtOAc (10 to 100%) in DCM to afford the title compound (284 mg, 90%) as a white solid. LCMS (M+H)+=303.

1. customThe ice bath was removed
2. stirringmixture was stirred at rt for 20 min, 50° C. for 2 h
3. waitrt for 10 h
4. additionThe reaction mixture was treated with water (8 mL)
5. extractionextracted with EtOAc (30 mL×3)
6. washThe combined organic layers were washed with brine (30 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel chromatography

ORD record

ord-ad90a23ba9304bb68f24948df58fd83a

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034900B2