Sodium Hydroxide → 3-(2,6-Difluorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylic acid

HRID 1047631Notes

Reaction equation

HRID 1047631 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([O:20]C)=[O:19])=[CH:15][CH:16]=2)[N:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:10]=1.[OH-].[Na+]>CO.O1CCCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[N:11]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[N:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66661289Methyl 3-(2,6-difluorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylate

Product 1

HCID 666616413-(2,6-Difluorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-(2,6-difluorophenyl)-1-(4-methylphenyl)-1H-indazole-6-carboxylate (101.2 mg, 0.267 mmol) was dissolved in methanol (1.30 mL) and tetrahydrofuran (1.90 mL). 1M sodium hydroxide (1.60 mL, 0.267 mmol) was added. The reaction mixture was heated to 50° C. and allowed to stir for 1.5 h. Reaction stopped, cooled to room temperature, quenched by addition of 1M hydrochloric acid (ca 1.60 mL) till pH<3, and the solvent evaporated under reduced pressure. The title compound (199.5 mg, 0.265 mmol, 99% yield, with 6 equivalents of sodium chloride) was recovered as a white solid. LC-MS: [M+1]=365.2.

Workup

  1. customReaction
  2. temperaturecooled to room temperature
  3. customquenched by addition of 1M hydrochloric acid (ca 1.60 mL) till pH<3
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-5e320fec21b742bf8279ab85db124930
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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