Tetrahydrofuran → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-isobutyramide

HRID 606921

Reaction equation

HRID 606921 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](OCC)(=O)C.[O:25]1[CH2:29][CH2:28][CH2:27]C1>>[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:29](=[O:25])[CH:28]([CH3:19])[CH3:27])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Product 1

HCID 67047872N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-isobutyramideYield 84%

Procedure

Add a solution of isobutynyl chloride (0.09 g, 1.08 mmol) dissolved in tetrahydrofuran to a solution of 5-(3-amino-4-fluorophenylethynyl) -nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous tetrahydrofuran and stir overnight at room temperature. Pour into ethyl acetate, wash with water and an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 95:5 dichloromethane:ethyl acetate, to give the title compound as a white solid (210 mg, 84%).

Workup

  1. washwash with water
  2. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 100:0 to 95:5 dichloromethane

Sources & evidence

ORD record
ord-2e81bec6aa2e4ab89ae75b6cede69755
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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