Methanesulfonyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamide

HRID 606956Notes

Reaction equation

HRID 606956 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1.O1CCCC1.O>[C:16]([C:15]1[CH:18]=[C:11]([C:10]#[C:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Product 1

HCID 67047582N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamideYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-(3-amino-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous pyridine. Add a solution of methanesulfonyl chloride (0.1 g, 0.88 mmol) in tetrahydrofuran to the reaction and stir overnight at room temperature. Concentrate and dissolve the crude reaction in ethyl acetate and water. Wash the organic layer with water, an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter, concentrate and purify (silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate), to give the title compound as a tan solid (50 mg, 20%).

Workup

  1. customto the reaction
  2. concentrationConcentrate
  3. dissolutiondissolve the crude
  4. customreaction in ethyl acetate
  5. washWash the organic layer with water
  6. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate)

Sources & evidence

ORD record
ord-e162a1bfde0440e4a4d47b5a19036340
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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