3-Bromoanisole → 5-Amino-1-(4-fluorophenyl)-4-(3-methoxybenzoyl)pyrazole

HRID 489840Notes

Reaction equation

HRID 489840 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.[NH2:11][C:12]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:15]=[CH:14][C:13]=1[C:24]([O:26]C1C=CC=CN=1)=S>O1CCCC1>[NH2:11][C:12]1[N:16]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[N:15]=[CH:14][C:13]=1[C:24](=[O:26])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 169713-BromoanisoleHCID 5462224MagnesiumHCID 537879785-Amino-1-(4-fluorophenyl)4-(2-pyridylthiocarboxy)pyrazole

Product 1

HCID 116020395-Amino-1-(4-fluorophenyl)-4-(3-methoxybenzoyl)pyrazoleYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into an oven dried flask containing magnesium turnings (0.408 g, 17 mmol) and tetrahydrofuran (10 ml) was added 3-bromoanisole (3.1 g, 17 mmol) and the reaction mixture was heated at reflux. After 2 h, the reaction mixture was cooled to room temperature and 5-amino-1-(4-fluorophenyl)-4-(2-pyridylthiocarboxy)pyrazole (1.5 g, 4.8 mmol) was added and the stirring was continued for 1 h. The reaction mixture was quenched with water and the product was extracted into ethyl acetate. The organic layer was washed with aqueous ammonium chloride and brine and dried over sodium sulfate. The organics were removed in vacuo and the residue was filtered and washed with hexane to give 5-amino-1-(4-fluorophenyl)-4-(3-methoxybenzoyl)pyrazole (1.20 g).

Workup

  1. customInto an oven dried flask
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux
  4. waitthe stirring was continued for 1 h
  5. customThe reaction mixture was quenched with water
  6. extractionthe product was extracted into ethyl acetate
  7. washThe organic layer was washed with aqueous ammonium chloride and brine
  8. dry with materialdried over sodium sulfate
  9. customThe organics were removed in vacuo
  10. filtrationthe residue was filtered
  11. washwashed with hexane

Sources & evidence

ORD record
ord-70d8940308cb4d6f99ea015487e3cb94
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Reaction notes

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