Potassium tert-butoxide → 1-(4-Fluorophenyl)-5-methoxy-1H-indazole

HRID 13188Notes

Reaction equation

HRID 13188 reaction equation
F[C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[CH:4]=[N:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.CC(C)([O-])C.[K+]>CN1C(=O)CCC1>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:2]3[C:3](=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[CH:4]=[N:5]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 668125981-(2-Fluoro-5-methoxybenzylidene)-2-(4-fluorophenyl)hydrazine

Product 1

HCID 593396221-(4-Fluorophenyl)-5-methoxy-1H-indazoleYield 36.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(2-fluoro-5-methoxybenzylidene)-2-(4-fluorophenyl)hydrazine (10 g, 38 mmol) and potassium tert. butoxide (5 g, 46 mmol) was stirred under argon atmosphere in NMP (50 mL) at 150° C. for 45 min. The reaction mixture was then cooled and poured with stirring into ice-water and extracted trice with ethyl acetate. The combined organic phases were washed with water and brine, and were then evaporated. The residue crystallized slowly from methanol-water to afford 1-(4-fluorophenyl)-5-methoxy-1H-indazole as beige crystals (3.32 g, 36%)

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionpoured
  3. extractionextracted trice with ethyl acetate
  4. washThe combined organic phases were washed with water and brine
  5. customwere then evaporated
  6. customThe residue crystallized slowly from methanol-water

Sources & evidence

ORD record
ord-03f3f205f7f34fdfbfb94ecf5bdb381b
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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