Hydrochloric Acid → (5-Bromopyridine-2,3-diyl)dimethanol

Temperature

23 °C

Sodium borohydride (15.9 g, 420 mmol) was added portionwise over 30 min to a solution of dimethyl 5-bromopyridine-2,3-dicarboxylate (20 g, 73 mmol) in ethanol (460 mL) precooled to 0° C. A solution of calcium chloride (23.3 g, 209 mmol) in 150 mL was added slowly at 0° C., and the reaction mixture was warmed to 23° C. and stirred overnight. Excess sodium borohydride was quenched by slow addition of aqueous 2 N HCl solution (230 mL, 460 mmol), followed by a stirring at 23° C. for 2 h. The mixture was concentrated to dryness. Saturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7 was reached. The aqueous mixture was extracted with 2-methyltetrahydrofuran (4×200 mL). The combined organic layers were dried over sodium sulfate then treated with a solution of 4 N HCl in dioxane (25 mL, 100 mmol). The resulting solid was filtered, washed with 2-methyltetrahydrofuran, and dried to give the title compound as a hydrochloride salt. MS: m/z=218.1 (M+1).

1. customprecooled to 0° C
2. customstirring at 23° C.
3. customfor 2 h
4. concentrationThe mixture was concentrated to dryness
5. additionSaturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7
6. extractionThe aqueous mixture was extracted with 2-methyltetrahydrofuran (4×200 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationThe resulting solid was filtered
9. washwashed with 2-methyltetrahydrofuran
10. customdried

ORD record

ord-ff9978fb63a84358b95ee9a721304f5a

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754096B2