Dimethylformamide → HCID 68183342, compound

Temperature

0 °C

To a 20 mL vial was added a solution of 2-bromo-4-(4-chlorophenyl)-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (0.0800 g, 0.233 mmol) in anhydrous N,N-dimethylformamide (3.00 mL, 38.7 mmol) and cooled to 0° C. NaH 60% in mineral oil (60:40, sodium hydride:Mineral Oil, 0.0500 g, 1.25 mmol) was added in portions and stirred for 10 minutes. Methyl iodide (0.0876 mL, 1.41 mmol) was added and the reaction mixture was slowly warmed to room temperature and allowed to stir for 1 hour. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride (5.00 mL) and diluted with EtOAc (10.00 mL). The mixture was successively washed with water (10.0 mL×2) and brine (10.0 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was wet loaded onto silica gel and then purified using a ISCO (4 g cartridge, gradient hexanes to 75% EtOAc over 30 min) to afford the product (0.0812 g, 78%) as a yellow oil. LC/MS (AA) ES+ 356, 358, 360. 1H NMR (dmso-d6, 400 MHz): d 7.43-7.37 (2H, m), 7.25-7.19 (2H, m), 6.98 (1H, s), 3.81-3.73 (1H, m), 3.66-3.58 (1H, m), 2.85 (3H, s).

1. temperaturethe reaction mixture was slowly warmed to room temperature
2. stirringto stir for 1 hour
3. customThe reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride (5.00 mL)
4. additiondiluted with EtOAc (10.00 mL)
5. washThe mixture was successively washed with water (10.0 mL×2) and brine (10.0 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. custompurified
10. customa ISCO (4 g cartridge, gradient hexanes to 75% EtOAc over 30 min)

ORD record

ord-17226b6b9ce8420b9ca34befd0e142f6

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765746B2