4-Fluorobenzenesulfonyl chloride → 4-fluoro-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamide

HRID 594113Notes

Reaction equation

HRID 594113 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH3:11])[C:7]([NH2:10])=[N:8][CH:9]=1)([CH3:3])[CH3:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:10][C:7]2[C:6]([CH3:11])=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][N:8]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chloride2×HCID 235305935-Isopropyl-3-methylpyridin-2-amine

Product 1

HCID 898763764-fluoro-N-(5-isopropyl-3-methylpyridin-2-yl)benzenesulfonamideYield 43.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-isopropyl-3-methylpyridin-2-amine (142 mg, 0.945 mmol) and 4-fluorobenzene-1-sulfonyl chloride (221 mg, 1.13 mmol) were dissolved in pyridine (3 mL) and left to stand overnight. Another 1 eq of 4-fluorobenzene-1-sulfonyl chloride was added to the mixture and the reaction left to stand for a further 6 hours. The reaction was concentrated in vacuo and the crude product extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid. The organic phase was then passed through a hydrophobic frit, concentrated in vacuo and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The relevant fractions were then combined and evaporated to give the title compound (127 mg). LCMS (2 min, formic) Rt 1.03 min, m/z (ES+) 309 (M+H).

Workup

  1. waitleft
  2. waitthe reaction left
  3. waitto stand for a further 6 hours
  4. concentrationThe reaction was concentrated in vacuo
  5. extractionthe crude product extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid
  6. concentrationconcentrated in vacuo
  7. custompurified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)
  8. customevaporated

Sources & evidence

ORD record
ord-782e2cbfd34f41dd8686a1667cd65ebd
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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