Ethyl 4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-carboxylate → HCID 66603517, compound

Temperature

0 °C

To a solution of ethyl(4-chloro-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)carboxylate (1.79 g; 5.78 mmol) in dry dichloromethane (18 mL) at −78° C. under nitrogen atmosphere was added a 1M solution of diisobutylaluminium hydride in dichloromethane (13.3 mL; 13.29 mmol). The resulting solution was stirred for 1.5 h and 1 h more at 0° C. The reaction mixture was quenched by adding 1N HCl carefully (17 mL) and the resulting mixture was vigorously stirred for 1 h. The phases were separated and the aqueous layer was extracted with dichloromethane. The organics were combined and washed with a Rochelle's salt solution and brine, dried over sodium sulphate, concentrated under reduced pressure to furnish 1.2 g (77%) of the title compound as an orange solid.

1. customThe reaction mixture was quenched
2. additionby adding 1N HCl carefully (17 mL)
3. stirringthe resulting mixture was vigorously stirred for 1 h
4. customThe phases were separated
5. extractionthe aqueous layer was extracted with dichloromethane
6. washwashed with a Rochelle's salt solution and brine
7. dry with materialdried over sodium sulphate
8. concentrationconcentrated under reduced pressure

ORD record

ord-da2d7e770b4b4025948c54dadc38c3d3

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785638B2