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

HRID 402356Notes

Reaction equation

HRID 402356 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]([CH3:27])[N:17]=[N:18][C:19]=2[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:9][CH:8]=1>O.C1COCC1.CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[N:18]=[N:17][N:16]([CH3:27])[C:15]=2[CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:28])=[O:5])=[CH:8][N:9]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 573341996-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester

Product 1

HCID 674979926-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acidYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (101 mg, 2.41 mmol) in water (3 mL) was added dropwise to a suspension of 6-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-nicotinic acid methyl ester (413 mg, 1.21 mmol) in THF (3 mL) and MeOH (0.6 mL). The reaction mixture was then stirred at room temperature for 1 h. The reaction mixture was then evaporated and the residue dissolved in water, acidified with HCl (1N), and the resulting precipitate filtered off to afford the title product (380 mg, 96%) as a white solid. MS: m/e=327.3 [M−H]−.

Workup

  1. customThe reaction mixture was then evaporated
  2. dissolutionthe residue dissolved in water
  3. filtrationthe resulting precipitate filtered off

Sources & evidence

ORD record
ord-df29c49d4dba42cdb996bb08d7fe6843
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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