Sodium Hydroxide → 3-({3-[2-(2,4,6-Trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoic acid

HRID 735452Notes

Reaction equation

HRID 735452 reaction equation
[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([O:27]CC)=[O:26])[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:33]([F:36])([F:35])[F:34])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.[OH-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:33]([F:34])([F:35])[F:36])=[CH:9][CH:10]=[CH:11]2)=[N:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86603014Ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoate

Product 1

HCID 866030173-({3-[2-(2,4,6-Trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoic acidYield 82.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}ethynyl)benzoate (0.19 g, 0.33 mmol) in CH3OH-THF (1:1, v/v) containing 1.0 mL of 1 N NaOH was stirred overnight at ambient temperature, then neutralized with dilute acid and partitioned with ethyl acetate and brine. The organic phase was dried (Na2SO4) and concentrated in vacuo to give 0.15 g of the title compound as a white solid.

Workup

  1. additionwith dilute acid
  2. custompartitioned with ethyl acetate and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a842b4d18a4f4496940ecc5d72208cc7
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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