Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)-6-(3-(trifluoromethyl)pyridin-2-yl)-1,2-dihydroindazol-3-one

HRID 270686Notes

Reaction equation

HRID 270686 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]4[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:14][CH:15]=3)[N:10]2COCC[Si](C)(C)C)=[CH:5][CH:4]=1.Cl>CCO>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([C:19]4[C:24]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:14][CH:15]=3)[NH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866128481,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one

Product 1

HCID 117505832-(4-(Trifluoromethyl)phenyl)-6-(3-(trifluoromethyl)pyridin-2-yl)-1,2-dihydroindazol-3-oneYield 45.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Step 6 (0.2 g), in a mixture of concentrated HCl (2 mL) and EtOH (3 mL), was heated at reflux for 1 h. The mixture was concentrated and the residue crystallized from EtOH/H2O to give 70 mg of product as a colourless solid. 1H NMR (360 MHz, CDCl3): 7.33 (1H, s), 7.39 (1H, d, J 8.0 Hz), 7.43 (1H, s), 7.5-7.55 (1H, m), 7.73 (2H, d, J 8.0 Hz), 7.99 (1H, d, J 8.0 Hz), 8.09 (2H, d, J 8.0 Hz), 8.14 (1H, d, J 8.0 Hz), 8.9 (1H, d, J 8.0 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. concentrationThe mixture was concentrated
  4. customthe residue crystallized from EtOH/H2O

Sources & evidence

ORD record
ord-a1bbeb0031884ed88efdacba56609217
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Reaction notes

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