Dimethylformamide → 5-Bromopyridine-2-carbaldehyde

To a solution of 5-bromo-2-iodopyridine (14.2 g, 50 mmol) in dry THF (160 mL) was added dropwise isopropylmagnesium (30 mL, 60 mmol) at −20 degrees Celsius under N2. After addition, the reaction mixture was stirred for about 2 h at the same temperature, and then DMF (5.11 g, 70 mmol) was added while keeping the temperature under 0 degrees Celsius. The reaction temperature was allowed to rise to rt and stirred for 1 hour, quenched with saturated ammonium chloride (10 ml), and then the solution pH was adjusted to 7-8 with 2.0 M HCl. The solvent was removed and extracted with ethyl acetate (2×200 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to obtain 8.5 g (90%) of a yellow solid product which was used directly in the next step without further purification. MS: calc'd 186 (MH+), exp 186 (MH+).

1. additionAfter addition
2. customunder 0 degrees Celsius
3. customto rise to rt
4. stirringstirred for 1 hour
5. customquenched with saturated ammonium chloride (10 ml)
6. customThe solvent was removed
7. extractionextracted with ethyl acetate (2×200 mL)
8. washThe combined organic layer was washed with brine
9. dry with materialdried with Na2SO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-912e4ecc23574b83886ac94ab1d44119

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977372B2