Sodium Hydroxide → 6-(4-Fluorophenyl)-2-(methoxymethyl)nicotinic acid

HRID 494202Notes

Reaction equation

HRID 494202 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[C:10]([CH2:19]Br)[N:9]=2)=[CH:4][CH:3]=1.[CH3:21][O-:22].[Na+].[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[C:10]([CH2:19][O:22][CH3:21])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 69039595Ethyl 2-(bromomethyl)-6-(4-fluorophenyl)-3-pyridinecarboxylate

Product 1

HCID 690388016-(4-Fluorophenyl)-2-(methoxymethyl)nicotinic acidYield 66.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 6-(4-fluorophenyl)-2-(bromomethyl)nicotinate (D85) (38 mg, 0.11 mmol) was treated with sodium methoxide (18 mg, 0.34 mmol) in methanol (1 ml) at room temperature for 1 h. 2M Sodium hydroxide solution was then added and the solution stirred for 1 h. The mixture was diluted with water and extracted with EtOAc which was dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (19 mg). MS(ES): MH+ 262, M-H+ 260.

Workup

  1. extractionextracted with EtOAc which
  2. dry with materialwas dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbffa6218ca04ef2894d1ff9878776a1
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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