Lithium hydroxide, monohydrate → 2'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid

HRID 2091820Notes

Reaction equation

HRID 2091820 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[F:29])[CH:11]=[C:12]([C:14]2[N:15]([CH:19]([CH3:21])[CH3:20])[N:16]=[CH:17][CH:18]=2)[CH:13]=1)=[O:7]>O.C1COCC1>[F:29][C:23]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=1[C:10]1[CH:11]=[C:12]([C:14]2[N:15]([CH:19]([CH3:21])[CH3:20])[N:16]=[CH:17][CH:18]=2)[CH:13]=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 577706482'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 577705982'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH hydrate (82 mg, 1.94 mmol) in H2O (7 mL) was added dropwise to a solution of 2′-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (524 mg, 1.49 mmol) in THF (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred until the reaction solution turned into clear. Solvent was removed under vacuum and the resulting aqueous solution was acidified by 10% HCl to pH=6˜7. The resulting precipitate was collected and dried to afford 2′-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4′-methyl-biphenyl-3-carboxylic acid (468 mg, 93%).

Workup

  1. customSolvent was removed under vacuum
  2. customThe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-654b0b3979fc4c908abf9c91c5a4efb6
Source dataset
uspto-grants-2013_05
Patent number
US08440673B2

Reaction notes

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