2,5-Dibromopyridine → HCID 86713197, compound

A solution of 2,5-dibromopyridine (5 g, 21 mmol), in dry toluene (200 mL, 0.1 M) is cooled to −75° C. under a blanket of nitrogen. 2.5 M n-BuLi in hexanes (16 mL, 25 mmol, 1.2 eq) is added drop-wise maintaining a temp less than −73° C. and the reaction mixture is stirred at −73° C. to −78° C. for 2 hours. The mixture is then added to a solution of tert-butyl (3-oxopropyl)carbamate (3.66 g, 21 mmol) in toluene (50 mL) at −78° C. The reaction mixture is stirred at −78° C. for 1 hour, before being allowed to warm slowly to room temperature and stirred overnight. The reaction mixture is quenched with saturated ammonium chloride solution (100 ml) and the toluene phase is separated and concentrated. The crude material is purified by chromatography (0-45% ethyl acetate in heptane) to give the title compound (3.1 g). MS (ESI+) m/z 331.0 [M+H].

1. temperaturemaintaining a temp less than −73° C.
2. stirringThe reaction mixture is stirred at −78° C. for 1 hour
3. stirringstirred overnight
4. customThe reaction mixture is quenched with saturated ammonium chloride solution (100 ml)
5. customthe toluene phase is separated
6. concentrationconcentrated
7. customThe crude material is purified by chromatography (0-45% ethyl acetate in heptane)

ORD record

ord-bb3fb0c0dbd44912b7b4204a4385efb7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206126B2