Acetonitrile → N-(5-Bromo-2-methoxypyridin-3-yl)methanesulfonamide
Reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH2:11])[C:6]([O:9][CH3:10])=[N:7][CH:8]=1.C(#N)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([NH:11][S:16]([CH3:15])(=[O:18])=[O:17])[C:6]([O:9][CH3:10])=[N:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
5-Bromo-2-methoxypyridin-3-amine hydrochloride (100 g, 1 wt, 1 eq) is charged to a CLR containing a mixture of acetonitrile (220 mL, 2.2 vols) and pyridine (101 mL, 1.01 vols, 99 g, 0.99 wt) at room temperature. Methanesulfonyl chloride (56.4 g, 0.564 wt, 1.18 eq) is then added to the mixture over 20 minutes whilst maintaining the temperature at 20° C. Having stirred at 20° C. for a further 1.5 hours, the mixture is sampled and analysed by HPLC. The completed reaction is quenched by the addition of water over 1 hour, maintaining the mixture at 20° C. and with increased stirrer speed. The resulting slurry is stirred for 17 hours and then filtered in vacuo. The cake is washed with 3:1 water:acetonitrile (2×50 mL, 2×0.5 vols) and then dried under vacuum at 40-45° C. to afford N-(5-bromo-2-methoxypyridin-3-yl)methanesulfonamide.
Workup
- additioncontaining
- aliquotthe mixture is sampled
- customThe completed reaction
- customis quenched by the addition of water over 1 hour
- temperaturemaintaining the mixture at 20° C.
- temperaturewith increased stirrer speed
- stirringThe resulting slurry is stirred for 17 hours
- filtrationfiltered in vacuo
- washThe cake is washed with 3:1 water
- dry with materialacetonitrile (2×50 mL, 2×0.5 vols) and then dried under vacuum at 40-45° C.
Sources & evidence
- ORD record
- ord-9ea6be8038b34fecaa3cb6505e9ffb4e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326987B2
Reaction notes
Loading…