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

HRID 1098949Notes

Reaction equation

HRID 1098949 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-bbd2af09d3d14c6481e03a8845da419e
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

Loading…