Lithium hydroxide, monohydrate → 5-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acid

HRID 402395Notes

Reaction equation

HRID 402395 reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[N:18]([CH3:29])[N:19]=[N:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=2)=[CH:11][N:10]=1)=[O:8])C>O.C1COCC1.CO>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]2[N:20]=[N:19][N:18]([CH3:29])[C:17]=2[CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]([C:7]([OH:8])=[O:6])=[N:10][CH:11]=2)=[N:23][CH:24]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 674981475-[5-(5-Fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 674979645-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acidYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (59 mg, 1.41 mmol) in water (1.8 mL) was added dropwise to a suspension of 5-[5-(5-fluoro-pyridin-2-yl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-pyridine-2-carboxylic acid ethyl ester (252 mg, 0.71 mmol) in THF (1.8 mL) and MeOH (0.4 mL). The reaction mixture was then stirred at room temperature for 2 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 (180 mg, 78%) as a white solid after trituration with ethyl acetate. MS: m/e=330.1 [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-ddd25abd85da469ab164647a8fbe7649
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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