Lithium hydroxide, monohydrate → 6-[3-(4-Fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid

HRID 402432Notes

Reaction equation

HRID 402432 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[N:16]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:17]=[N:18][C:19]=2[CH3:20])=[N:9][CH:8]=1>O.C1COCC1.CO>[F:27][C:24]1[CH:25]=[CH:26][C:21]([N:16]2[C:15]([CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:28])=[O:5])=[CH:8][N:9]=3)=[C:19]([CH3:20])[N:18]=[N:17]2)=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 573354046-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 674987456-[3-(4-Fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acidYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (143 mg, 3.39 mmol) in water (5.8 mL) was added dropwise to a suspension of 6-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester (581 mg, 1.7 mmol) in THF (5.8 mL) and methanol (2 mL). The reaction mixture was then stirred at room temperature for 30 min and was then evaporated and the residue dissolved in water, acidified with HCl (1N), and the resulting precipitate filtered off to afford the title product (538 mg, 97%) as a white solid. MS: m/e=327.2 [M−H]−.

Workup

  1. customwas then evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-35ad5a69ec66461f81403a4918810da5
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

Loading…