Lithium hydroxide, monohydrate → 3-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid

HRID 2224655Notes

Reaction equation

HRID 2224655 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[N:18][O:19][C:20]=3[CH3:21])=[O:15])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].O[Li].O>C1COCC1.O>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:17]2[C:16]([C:14]([C:9]3[C:8]4[C:12](=[CH:13][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=4)[NH:11][CH:10]=3)=[O:15])=[C:20]([CH3:21])[O:19][N:18]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 691113023-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 691119953-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.7 g (1.85 mmol) 3-[3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid methyl ester in 12 mL of THF and 6 mL of H2O, was added 0.39 g (9.25 mmol) LiOH.H2O in one portion. The reaction mixture was heated under reflux for 16 h. After the evaporation the mixture was extracted with Et2O (10 mL), and acidified to pH=2-3 with 2 N HCl. The resulting solid was filtered off, washed with water and dried to give 0.65 g of the title compound (intermediate 1) in 97% yield as a white solid. (m/e): 365.1 (MH+; 100%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. customAfter the evaporation the mixture
  4. extractionwas extracted with Et2O (10 mL)
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-5ef14da6976c470ab049c628dbf01cf3
Source dataset
uspto-grants-2008_05
Patent number
US07378435B2

Reaction notes

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