4-Fluorobenzenesulfonyl chloride → N-(3,5-dimethylpyridin-2-yl)-4-fluorobenzenesulfonamide

HRID 594103Notes

Reaction equation

[CH3:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH3:1][C:2]1[C:3]([NH:9][S:17]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred solution of 3,5-dimethylpyridin-2-amine (129 mg, 1.056 mmol) in pyridine (5 mL) at room temperature, was added 4-fluorobenzene-1-sulfonyl chloride (205 mg, 1.056 mmol). The reaction mixture was stirred at 20° C. for 30 minutes, then left to stand for 16 hours. Additional 4-fluorobenzene-1-sulfonyl chloride (205 mg, 1.056 mmol) was then added and the reaction stirred for an additional 4 hours. The reaction mixture was concentrated in vacuo and purified by passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge eluting with methanol, followed by a sulphonic acid (SCX) SPE cartridge eluting with methanol then 2M ammonia/methanol. Concentration of the product-containing fractions provided the title compound (84.1 mg) as a yellow oil. LCMS (2 min, formic) Rt 0.89 min, m/z (ES+) 281 (M+H).

Workup

waitleft
waitto stand for 16 hours
stirringthe reaction stirred for an additional 4 hours
concentrationThe reaction mixture was concentrated in vacuo
custompurified
extractionby passing through an aminopropyl (NH2) solid phase extraction (SPE) cartridge
washeluting with methanol
washeluting with methanol

Sources & evidence

ORD record: ord-413c661d6cc94633b6f614c4ceb3ac46
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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