Acetyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-acetamide

HRID 606955Notes

Reaction equation

HRID 606955 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].[C:19](Cl)(=[O:21])[CH3:20]>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][C:19](=[O:21])[CH3:20])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Product 1

HCID 67048361N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-acetamideYield 81%

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. A solution of acetyl chloride (0.07 g, 0.88 mmol) in tetrahydrofuran is added to the reaction and stirred 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 white solid (180 mg, 81%).

Workup

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

Sources & evidence

ORD record
ord-9ef8a5587dac4043a119d3848e1ccba0
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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