1-(2-Fluoro-4-iodophenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide → 3-Acetyl-1-(2-fluoro-4-iodophenyl)-5-methoxypyridazin-4(1H)-one

HRID 1895119Notes

Reaction equation

HRID 1895119 reaction equation
[CH3:1][Mg+].[Br-].[F:4][C:5]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:6]=1[N:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15](=[O:20])[C:14]([C:21](N(OC)C)=[O:22])=[N:13]1>C1COCC1>[C:21]([C:14]1[C:15](=[O:20])[C:16]([O:18][CH3:19])=[CH:17][N:12]([C:6]2[CH:7]=[CH:8][C:9]([I:11])=[CH:10][C:5]=2[F:4])[N:13]=1)(=[O:22])[CH3:1]

Participants

4

Reactant 2

HCID 866439311-(2-Fluoro-4-iodophenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 594362253-Acetyl-1-(2-fluoro-4-iodophenyl)-5-methoxypyridazin-4(1H)-oneYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1 M solution in THF, 70 mL, 70 mmol) was added dropwise at −78° C. to a solution of 1-(2-fluoro-4-iodophenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (9.96 g, 23 mmol) in THF (250 mL). After stirring for 1 h, the reaction mixture was quenched with 1 M HCl aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with AcOEt and recrystallized from MeOH to give the title compound (2.05 g, 23% yield) as pale yellow crystals: mp 196-198° C.; 1H NMR (300 MHz, CDCl3): δ ppm 2.67 (3H, s), 3.90 (3H, s), 7.36-7.41 (1H, m), 7.66-7.71 (2H, m), 7.73 (1H, d, J=2.6 Hz). Anal. Calcd for C13H10FIN2O3: C, 40.23; H, 2.60; N, 7.22. Found: C, 40.25; H, 2.87; N, 7.28.

Workup

  1. customthe reaction mixture was quenched with 1 M HCl aqueous solution
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with AcOEt
  8. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-9dd06ce2aac74852853c1fcb6ab89cb4
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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