Methanol → N-[1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

Temperature

0 °C

To a solution of 2-amino-2-(6-bromo-pyridin-2-yl)-propan-1-ol (4.9 g, 21.2 mmol) in DCM (50 ml) was added K2CO3 (5.86 g, 42.4 mmol). The reaction mixture was cooled to 0° C. and 2-chloroacetyl chloride (2.55 ml, 3.59 g, 31.8 mmol) was added dropwise. The reaction mixture was allowed to warm to rt and to stir for 5 h. MeOH (20 ml) was added and stirring was continued at rt for 1 h. The reaction mixture was diluted with H2O and DCM, the phases were separated and the aq. phase was twice extracted with DCM. The combined org. phases were dried over Na2SO4, filtered and the solvent was removed to leave N-[1-(6-bromo-pyridin-2-yl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide as an orange oil. HPLC RtH4=0.73-0.77 min; ESIMS: 307, 309 [(M+H)+]; 1H NMR (400 MHz, DMSO-d6): δ 8.35 (s, 1H), 7.70-7.66 (m, 1H), 7.48 (dd, 1H), 7.38 (dd, 1H), 5.05-5.02 (m, 1H), 4.14 (s, 2H), 3.68-3.66 (m, 2H), 1.55 (s, 3H).

1. temperatureto warm to rt
2. stirringstirring
3. waitwas continued at rt for 1 h
4. customthe phases were separated
5. extractionthe aq. phase was twice extracted with DCM
6. dry with materialphases were dried over Na2SO4
7. filtrationfiltered
8. customthe solvent was removed

ORD record

ord-fabccc9971e94f8482b42b9f9b179055

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865712B2