Pyridine → N-[5-(5-Chloropyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamide

HRID 606948Notes

Reaction equation

HRID 606948 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].[Cl:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21]2[CH:22]=[CH:23][C:24]([F:28])=[C:25]([NH2:27])[CH:26]=2)[CH:16]=[N:17][CH:18]=1>ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21]2[CH:22]=[CH:23][C:24]([F:28])=[C:25]([NH:27][S:8]([CH3:7])(=[O:10])=[O:9])[CH:26]=2)[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 670475245-(5-Chloropyridin-3-ylethynyl)-2-fluorophenylamine

Product 1

HCID 67048459N-[5-(5-Chloropyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add pyridine (193 mg, 2.44 mmol) followed by methanesulfonyl chloride (127 mg, 1.11 mmol) to a solution of 5-(5-chloropyridin-3-ylethynyl)-2-fluorophenylamine, (prepared as described in EXAMPLE 190), (275 mg, 1.11 mmol) in dichloromethane (10 mL) at 0° C. under nitrogen. Warm to room temperature and stir 20 h. Add additional methanesulfonyl chloride (32 mg, 0.28 mmol). Stir at room temperature for 2 h. Concentrate and purify by silica gel chromatography, eluting with 3:1 ethyl acetate:hexanes, to give the title compound as a white solid (330 mg, 92%).

Workup

  1. stirringStir at room temperature for 2 h
  2. concentrationConcentrate
  3. custompurify by silica gel chromatography
  4. washeluting with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-adf5c525d68a481ead4c7c2d8b0f3132
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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