Stannous Chloride → 2-(4-Chloro-phenyl)-5,6-difluoro-2H-indazol-3-ylamine

HRID 1690538Notes

Reaction equation

HRID 1690538 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:14]=2[C:15]#[N:16])=[CH:7][CH:6]=1>C(O)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([NH2:16])=[C:14]3[C:13]([CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17]3)=[N:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 866402642-(4-Chloro-phenylazo)-4,5-difluoro-benzonitrile

Product 1

HCID 669051692-(4-Chloro-phenyl)-5,6-difluoro-2H-indazol-3-ylamineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride (11.4 g, 60 mmol) was added to a solution of 2-(4-chloro-phenylazo)-4,5-difluoro-benzonitrile (3.3 g, 12 mmol) in ethanol (91 ml) under an argon atmosphere. The suspension was heated under reflux conditions for 16 h and the solvent removed under reduced pressure. The residue was taken up in half saturated aqueous NaHCO3 solution/EtOAc 1/1, the layers were separated and filtered separately over dicalite. The filtrate of the aqueous layer was extracted two times with EtOAc, the organic layers were combined, washed with ice water and dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound (3.2 g, 11 mmol; 95%) as light brown solid which was used in the next step without further purification. MS: m/e=280.0 [M+H+].

Workup

  1. temperatureThe suspension was heated under reflux conditions for 16 h
  2. customthe solvent removed under reduced pressure
  3. customthe layers were separated
  4. filtrationfiltered separately over dicalite
  5. extractionThe filtrate of the aqueous layer was extracted two times with EtOAc
  6. washwashed with ice water
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f8617443eff94a94b37d845d281c943a
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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