Lithium hydroxide, monohydrate → 6-((4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinic acid

HRID 402367Notes

Reaction equation

HRID 402367 reaction equation
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[N:13][N:14]([CH3:28])[C:15]=1[CH2:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][N:19]=1>O.C1COCC1>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[N:12]=[N:13][N:14]([CH3:28])[C:15]=1[CH2:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57334494Methyl 6-((4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinate

Product 1

HCID 674983346-((4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinic acidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (23 mg, 0.56 mmol) in water (0.8 mL) was added dropwise to a suspension of methyl 6-((4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methoxy)nicotinate (95 mg, 0.28 mmol) in THF (0.8 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 (68 mg, 75%) as a white solid. MS: m/e=327.1 [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-5b67d68bba274a10a83b6f2d7a38d60b
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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