4-Toluenesulfonyl chloride → N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

HRID 1971630Notes

Reaction equation

HRID 1971630 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 57607460N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-5-fluoropyridine (4.0 g, 0.036 mol) was dissolved in pyridine (40 mL) and p-toluenesulfonyl chloride (7.5 g, 0.039 mol) was added. The reaction was heated at 80° C. for 24 hours then cooled and the pyridine was removed under vacuum. The residue was partioned between water (100 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was washed (3×100 mL) with water then dried and solvent stripped to give clean N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide 1 Rf 0.42, 50% E/H; MS m/z 267 (M+H).

Workup

  1. temperaturethen cooled
  2. customthe pyridine was removed under vacuum
  3. customThe layers were separated
  4. washthe organic layer was washed (3×100 mL) with water
  5. customthen dried

Sources & evidence

ORD record
ord-2c6765f9cf1a419c9e947b6f06cdc0a2
Source dataset
uspto-grants-2013_04
Patent number
US08431608B2

Reaction notes

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