N-bromobutanimide → HCID 118079918, compound

A solution of (S)-2-(3-nitropyridin-2-ylamino)propane-1-ol (4.88 g, 24.75 mmol) in acetonitrile (50 mL) was cooled to 0° C. and treated with N-bromosuccinimide (4.40 g, 24.75 mmol) in one portion. The ice bath was left in place and allowed to slowly expire over 15 h. The solution was then concentrated under reduced pressure in order to remove most (>90%) of the acetonitrile. The concentrated solution was dissolved in ethyl acetate and washed with half-saturated aqueous sodium bicarbonate solution (2×75 mL) and 5% aqueous sodium chloride solution (1×75 mL). The ethyl acetate solution was then concentrated under reduced pressure to afford (S)-2-(5-bromo-3-nitropyridin-2-ylamino)propane-1-ol (7.11 g) as a dark yellow solution which was used in the next step without purification. MS (ESI, pos. ion) m/z 276. 278 [M+1]+.

1. concentrationThe solution was then concentrated under reduced pressure in order
2. customto remove most (>90%) of the acetonitrile
3. dissolutionThe concentrated solution was dissolved in ethyl acetate
4. washwashed with half-saturated aqueous sodium bicarbonate solution (2×75 mL) and 5% aqueous sodium chloride solution (1×75 mL)
5. concentrationThe ethyl acetate solution was then concentrated under reduced pressure

ORD record

ord-bb255532a3924612b3a7dcfdfeb8f4f8

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2