Methanol → HCID 66644519, compound

HRID 1962977Notes

Reaction equation

HRID 1962977 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][C:22]([F:25])=[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>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:14]2[C:13]([CH2:12][O:11][C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[C:17]([CH3:18])[O:16][N:15]=2)=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 66644374HCID 66644374, compound

Product 1

HCID 66644519HCID 66644519, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid methyl ester (540 mg, 1.42 mmol) in THF (5.4 mL) was added a solution of lithium hydroxide monohydrate (118 mg, 2.83 mmol) in water (5.4 mL) followed by methanol (2 mL) and the resulting mixture stirred at room temperature overnight. 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 (321 mg, 69%) which was obtained as a white solid. MS: m/e=328.3 [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-161836684981414aa65b3724cf7e93cd
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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