4-Fluorobenzenesulfonyl chloride → 4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594117Notes

Reaction equation

HRID 594117 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([CH3:3])[CH3:2].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][N:8]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 179858055-(Propan-2-yl)pyridin-2-amine

Product 1

HCID 898759264-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-isopropylpyridin-2-amine (300 mg, 2.20 mmol) and 4-fluorobenzene-1-sulfonyl chloride (557 mg, 2.86 mmol) were dissolved in pyridine (3 mL) and left to stand overnight. The reaction mixture was concentrated in vacuo and the crude product extracted to the organic phase of an acidic workup between ethyl acetate and 5% citric acid. The organic phase was passed through a hydrophobic frit and concentrated in vacuo to give the title compound (430 mg). LCMS (2 min, formic) Rt 0.90 min, m/z (ES+) 295 (M+H).

Workup

  1. waitleft
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe crude product extracted to the organic phase of an acidic workup between ethyl acetate and 5% citric acid
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb801e81b9cb49548a2316c7451a05f4
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

Loading…