Sodium borohydride → HCID 59674980, compound

HRID 1391504Notes

Reaction equation

HRID 1391504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=3[F:23])[C:9]=2[C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[CH:15][C:14]=3[F:23])[C:9]=2[CH:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[OH:25])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67313333HCID 67313333, compound

Product 1

HCID 59674980HCID 59674980, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 56 mg (0.13 mmol) of 5-(3-chlorophenyl)-3-(2-fluoro-5-trifluoromethyl-phenyl)-4-[(3-pyridyl)carbonyl]isoxazole in 2 mL of ethanol was added 24 mg (0.63 mmol) of sodium borohydride. After 2 hrs at room temperature, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated sodium chloride and was dried over magnesium sulfate. The drying agent was filtered off, and solvent was removed by rotoevaporation. The residue was purified by prepTLC to give 44 mg (0.098 mmol) of 5-(3-chlorophenyl)-3-(2-fluoro-5-trifluoromethylphenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole. 1H NMR (CDCl3): δ 6.01 (s, 1), 7.01 (m, 1), 7.83 (m, 1), 8.27 (m, 1), and 8.35 ppm (br s, 1). MS m/z: 449.0 (M+H).

Workup

  1. washThe solution was washed with saturated sodium chloride
  2. dry with materialwas dried over magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. customsolvent was removed by rotoevaporation
  5. customThe residue was purified by prepTLC

Sources & evidence

ORD record
ord-546af7d801774eaf883bad665990f4eb
Source dataset
uspto-grants-2008_03
Patent number
US07338967B2

Reaction notes

Loading…