3-Acetyl-N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-benzenesulfonamide → N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-3-(1-hydroxy-1-methyl-ethyl)-benzenesulfonamide

HRID 1898248Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([S:11]([NH:14][C:15]2[C:16]([Br:22])=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][C:9]=1[Cl:10])(=[O:3])[CH3:2].[CH3:23][Mg]Br>C1COCC1.C(OCC)C>[Br:22][C:16]1[C:15]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([C:1]([OH:3])([CH3:23])[CH3:2])[CH:5]=2)(=[O:12])=[O:13])=[CH:20][C:19]([Cl:21])=[CH:18][N:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

365 mg (0.86 mmol) of 3-acetyl-N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-benzenesulfonamide was dissolved in 3 mL of anhydrous THF and cooled down under nitrogen atmosphere to −78° C. To that solution 0.86 mL of 3M methylmagnesium bromide solution in diethyl ether was added dropwise. The solution was allowed to warm up to 0° C. and was then quenched with aqueous ammonium chloride and extracted with DCM. The organic layer was evaporated under reduced pressure and purified on silica using 5-40% ethyl acetate in hexanes to yield 288 mg of a white solid. LC-MSD, m/z for C14H13BrCl2N2O3S [M+H]+=438.9, 440.9, 442.9.

Workup

temperatureto warm up to 0° C.
customwas then quenched with aqueous ammonium chloride
extractionextracted with DCM
customThe organic layer was evaporated under reduced pressure
custompurified on silica using 5-40% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-d5c26c3f508344bb95d1e6a8012efda9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519135B2

Reaction notes

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