Pyridine → 3-cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide

HRID 2178117Notes

Reaction equation

HRID 2178117 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10](Cl)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[F:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=1.N1C=CC=CC=1>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([F:14])=[CH:20][N:19]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27377012-Amino-5-fluoropyridineHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Product 1

HCID 594366003-cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyano-4-fluorobenzene-1-sulfonyl chloride (25 g, 114 mmol) was added to a solution of 5-fluoropyridin-2-amine (16.85 g, 150 mmol) and pyridine (23.7 g, 300 mmol) in dichloromethane (500 mL) at room temperature. The resulting mixture was stirred at room temperature for 3 hours. After evaporating the solvent the solid was stirred in diluted aqueous hydrochloric acid (2N, 400 mL) for 16 hours. The reaction mixture was filtered, washed with water (200 mL) and dried under high vacuum to afford the title compound as an orange solid (30.9 g, 98%).

Workup

  1. customAfter evaporating the solvent the solid
  2. stirringwas stirred in diluted aqueous hydrochloric acid (2N, 400 mL) for 16 hours
  3. filtrationThe reaction mixture was filtered
  4. washwashed with water (200 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-6fd9639ef0a6468bab84c907ec7e4f6b
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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