3-(Bromomethyl)pyridine → HCID 86591862, compound

Participants

Reaction Conditions

Reaction Steps

Step 49a) To a solution of cyclopropylsulfonylamine tert-butyl carbamate (105 g, 4.52 mmol) in THF (9 mL) cooled to −78° C., was added n-BuLi (6.2 mL, 9.2 mmol, 1.6 M in hexane). The mixture was stirred for 1 h at −78° C., and fresh ether solution (2 mL) of 3-(bromomethyl)pyridine was injected in one portion. The fresh 3-(bromomethyl)pyridine was made from 1.5 g (5.9 mmol) of 3-(bromomethyl)pyridine hydrobromide tributed between aqueous sodium bicarbonate and ether. The ether layer was quickly separated, dried (MgSO4), and concentrated in vacuo till about 2 mL liquid left. The reaction mixture was stirred for 4 min, changed the bath into ice water, and stirred for 1 h. The reaction mixture was diluted with pH 4.0 buffer, adjusted pH to 4, and extracted with EtOAc. The extraction was dried (MgSO4), concentrated, and purified by prep-HPLC (sovent B: 0 to 80%) to afford 0.61 g mixture with 1-(3-pyridyl)-cyclopropanesulfonamide-tert-butylcarbamate, and the mixture was used in next step.

Provenance & Evidence