Methanol → 5-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid

HRID 1962958Notes

Reaction equation

HRID 1962958 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+].CO>C1COCC1.O>[CH3:18][C:17]1[O:16][N:15]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:13]=1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 666445115-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 666446485-(5-Methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acidYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid methyl ester (56 mg, 0.17 mmol) in THF (0.6 mL) was added a solution of lithium hydroxide monohydrate (15 mg, 0.34 mmol) in water (0.6 mL) followed by methanol (0.2 mL) and the resulting mixture stirred at room temperature for 2 h. The mixture was then evaporated and acidified with HCl (1 N) and the mixture cooled to 0° C. for 30 min. A solid formed which was filtered off, washed with water and dried to afford the title compound (41 mg, 76%) which was obtained as a white solid. MS: m/e=310.3 [M−H]−.

Workup

  1. customThe mixture was then evaporated
  2. temperaturethe mixture cooled to 0° C. for 30 min
  3. customA solid formed which
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-247c0d8a68834b4ca550dd57de61aa62
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

Loading…