HCID 67131071, compound → HCID 67131189, compound

HRID 1678649Notes

Reaction equation

HRID 1678649 reaction equation
Cl[C:2]1[N:3]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[C:8]([F:11])[C:7]([F:12])=[CH:6]2>C(O)(=O)C.[Zn]>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([N:3]2[CH:2]=[C:10]3[C:5]([CH:6]=[C:7]([F:12])[C:8]([F:11])=[CH:9]3)=[N:4]2)=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 67131071HCID 67131071, compound

Product 1

HCID 67131189HCID 67131189, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (14.7 g, 225 mmol) was added to a suspension of 3-chloro-2-(4-chloro-phenyl)-5,6-difluoro-2H-indazole (16.8 g, 56 mmol) in acetic acid (118 ml). The suspension was heated under reflux conditions for 2 h. The hot solution was filtered, the filtrate was poured onto ice water/brine 1/1 and extracted two times with TBME. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. The solvent was removed under reduced pressure to give a brown solid which was crystallized from dichloromethane/n-heptane to give the title compound (12.1 g, 46 mmol; 81%) as brown crystals. MS: m/e=265.1 [M+H+].

Workup

  1. temperatureThe suspension was heated under reflux conditions for 2 h
  2. filtrationThe hot solution was filtered
  3. additionthe filtrate was poured onto ice water/brine 1/1
  4. extractionextracted two times with TBME
  5. washThe combined extracts were washed with ice water/brine 1/1
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customto give a brown solid which
  9. customwas crystallized from dichloromethane/n-heptane

Sources & evidence

ORD record
ord-7cd52d58763e461ba45732d42271b3ae
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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