Triethylamine → (2,6-dibromopyridin-3-yl)methanol

To a mixture of 1.51 g of 2,6-dibromonicotinic acid (Helvetica Chimica Acta, 1976, 59, 229), 0.72 ml of triethylamine and 30 ml of tetrahydrofuran was added 0.57 ml of ethyl chloroformate at 0° C. After stirring at room temperature for 30 minutes, an insoluble matter was filtered. To the filtrate was added 30 ml of tetrahydrofuran, and then 717 mg of sodium borohydride was added thereto. To this mixture was added 13 ml of methanol at 5° C. followed by stirring for 15 minutes. The reaction mixture was diluted with ethyl acetate and then washed with an aqueous solution of saturated ammonium chloride and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the title compound.

1. filtrationan insoluble matter was filtered
2. additionTo the filtrate was added 30 ml of tetrahydrofuran
3. addition717 mg of sodium borohydride was added
4. additionTo this mixture was added 13 ml of methanol at 5° C.
5. stirringby stirring for 15 minutes
6. additionThe reaction mixture was diluted with ethyl acetate
7. washwashed with an aqueous solution of saturated ammonium chloride and brine
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated

ORD record

ord-68ea28f8a3ef4bfdb96efc5875d82ba5

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834018B2