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

HRID 46322

Reaction equation

HRID 46322 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)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyano-4-fluorobenzenesulfonyl chloride (5 g, 20 mmol), 5-fluoropyridin-2-amine (3.37 g, 30 mmol) and pyridine (4.87 mL, 60 mmol) in dichloromethane (100 mL) were stirred at room temperature for 2 hours before concentrating in vacuo. The residue was triturated in hydrochloric acid (2 N aqueous solution, 100 mL) for 16 hours. The precipitate was filtered to afford the title compound as a pale pink solid, 6.1 g.

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was triturated in hydrochloric acid (2 N aqueous solution, 100 mL) for 16 hours
  3. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-a8c4714f0d7c45e3a9003b24c6a5e230
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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