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 1407111Notes

Reaction equation

HRID 1407111 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: 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-b5621733e20c4aa2879e84c3c061cbe9
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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