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

HRID 402423Notes

Reaction equation

HRID 402423 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C: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[C:14]#[C: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 674980856-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acid methyl ester

Product 1

HCID 674991796-[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acidYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (30 mg, 0.72 mmol) in water (0.9 mL) was added dropwise to a suspension of 6-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylethynyl]-nicotinic acid methyl ester (121 mg, 0.36 mmol) in THF (0.9 mL) and methanol (0.2 mL). The reaction mixture was then stirred at room temperature for 18 h 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 (89 mg, 77%) as a light yellow solid after trituration with ethyl acetate. MS: m/e=321.1 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-e86b2a0467a74cddb7d4d39a5f9e5e07
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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