Diisobutylaluminumhydride → (6-Bromo-4-iodopyridin-3-yl)methanol

To a solution of methyl 6-bromo-4-iodonicotinate (500 mg, 1.0 mmol) in methylene chloride (6 mL) cooled at 0° C. was added a 1.0M solution of diisobutylaluminum hydride in tetrahydrofuran (5.85 mL) dropwise over 5 minutes. The reaction mixture was stirred at this temperature for 30 minutes and then quenched by dropwise addition of a 1.0M solution of citric acid in water (1 mL). The reaction mixture was diluted with dichloromethane (20 mL) and washed with water (15 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a white solid (430 mg, 90%), which was used in the next step without further purification.

1. customquenched by dropwise addition of a 1.0M solution of citric acid in water (1 mL)
2. additionThe reaction mixture was diluted with dichloromethane (20 mL)
3. washwashed with water (15 mL)
4. customThe organic layer was separated
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customto afford a residue that
9. customwas purified by flash chromatography (silica, 12 g, ISCO, 0-50% ethyl acetate in heptane)

ORD record

ord-9e6e9adebce441f79cbea34ea4a14eac

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623889B2