Dimethyl Sulfoxide → HCID 18516175, compound

Temperature

-78 °C

To a stirred solution of oxalyl chloride (0.10 mL, 1.17 mmol) in anhydrous dichloromethane (1 mL) at −78° C. was added DMSO (0.19 mL, 2.65 mmol). After 20 minutes, a solution of dimethylethyl 4-(hydroxymethyl)-thieno[2,3-c]pyridine-2-carboxylate (0.28 g, 1.06 mmol) in anhydrous dichloromethane (4 mL) was added dropwise. The reaction was stirred 1 hours at −78° C. then treated with triethylamine (0.74 mL, 5.30 mmol). After 5 minutes, reaction was allowed to warm to room temperature over 30 minutes. The reaction was quenched with water (5 mL) and partitioned between dichloromethane (50 mL) and 50% sat. aq NaHCO3 (50 mL). The organic phase was washed with 50% sat. aq NaHCO3 (1×50 mL), dried (Na2SO4), filtered, and concentrated and dried in a desiccator to yield the title as a solid (0.25 g, 90%).

1. waitAfter 5 minutes
2. customreaction
3. temperatureto warm to room temperature over 30 minutes
4. customThe reaction was quenched with water (5 mL)
5. custompartitioned between dichloromethane (50 mL) and 50% sat. aq NaHCO3 (50 mL)
6. washThe organic phase was washed with 50% sat. aq NaHCO3 (1×50 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customdried in a desiccator

ORD record

ord-042b2f2121804e35a409394709cfd2c7

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06579882B2