Bromide ion → HCID 86695485, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of N-((5-(4-((1R,2S)-2-amino-3-fluoro-1-hydroxypropyl) phenyl) pyridin-2-yl) methyl)methanesulfonamide (800 mg, 2.26 mmol) in ethylacetate/aqueous NaHCO3 (1:1) (10 mL) is slowly added bromoacetyl bromide (900 mg, 4.5 mmol) over a period of 20 minutes. Organic layer is separated and aqueous layer extracted with ethyl acetate (3×10 mL). Combined extract is dried over Na2SO4 and concentrated to get crude product. m/z (CI) M+H 474. A mixture of crude bromide (500 mg) and sodium azide (470 mg, 7.0 mmol) in dimethylformamide (6 mL) is heated for 30 min at 50° C. Reaction is cooled, diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). Combined extract is dried over Na2SO4, concentrated under vacuum and then obtained crude product purified on silica gel column using 0 to 5% methanol/CH2Cl2 to give the title compound (300 mg): 1H NMR (400 MHz, DMSO-d6) 2.95 (s, 3H), 3.71-3.87 (m, 2H), 4.22-4.42 (m, 4H), 4.47-4.58 (m, 0.5H), 4.50-4.70 (m, 0.5H), 4.83-4.93 (m, 1H), 5.83-5.93 (m, 1H), 7.47 (d, 2H), 7.54 (d, 1H), 7.64-7.77 (m, 3H), 8.06-8.20 (m, 2H), 8.83 (d, 1H). m/z (CI) M+H 437.

Provenance & Evidence