(4-Fluorophenyl)hydrazine → 3-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

HRID 2233735

Reaction equation

HRID 2233735 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=1>C(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][C:7]2[C:18]3[C:17](=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=3)[NH:20][C:8]=2[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69982(4-Fluorophenyl)hydrazineHCID 2398741-(4-Chlorophenoxy)acetone

Product 1

HCID 117018033-(4-chlorophenoxy)-5-fluoro-2-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Chloro-phenoxy)-propan-2-one (2.05 g) was added to a stirred solution of (4-fluoro-phenyl)-hydrazine (1.4 g) in ethanol (30 ml) at RT. After 2 h, the solvent was removed under reduced pressure and the residue dissolved in DCM (30 ml). Phosphorus trichloride (1.06 ml) was added dropwise to the solution and after stirring at RT for 16 h the reaction was quenched with aq. sodium hydrogencarbonate solution. The mixture was extracted with DCM, the organics washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane. Yield 0.75 g

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in DCM (30 ml)
  3. additionPhosphorus trichloride (1.06 ml) was added dropwise to the solution
  4. customwas quenched with aq. sodium hydrogencarbonate solution
  5. extractionThe mixture was extracted with DCM
  6. washthe organics washed with water
  7. customdried
  8. customevaporated under reduced pressure
  9. customThe residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane

Sources & evidence

ORD record
ord-58e7debb475743fc80e44a9d88bdd9ce
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Linked notes

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