Potassium Hydroxide → 1,2-Dihydro-6-bromo-2-(4-trifluoromethylphenyl)-3H-indazol-3-one

HRID 270683Notes

Reaction equation

HRID 270683 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:6]=2Cl.[OH-:22].[K+]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:22])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 692016176-Bromo-3-chloro-2-(4-trifluoromethylphenyl)-2H-indazole

Product 1

HCID 692027741,2-Dihydro-6-bromo-2-(4-trifluoromethylphenyl)-3H-indazol-3-oneYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product of Step 3 (2.4 g, 0.0064 mol) in 1M KOH in MeOH (16 mL) was heated at 150° C. in a sealed tube via microwave irradiation for 15 min. The mixture was then concentrated, diluted with H2O, acidified with 1N HCl and the resulting precipitate collected by filtration to give 1.0 g (44% yield) of product. 1H NMR (360 MHz, CDCl3): 7.37 (1H, dd, J 1.4 and 8.5 Hz), 7.66 (1H, d, 1.4 Hz), 7.73 (1H, d, 8.5 Hz), 7.89 (2H, d, 8.5 Hz), 8.13 (2H, d, 8.5 Hz), 11.0 (1H, s).

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with H2O
  3. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-b097dd65eaac4012b241275d62a0edd4
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Reaction notes

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