Sodium borohydride → HCID 59674980, compound

HRID 1672422Notes

Reaction equation

HRID 1672422 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-50afb4d389c948ce8e54a35e645fffa9
Source dataset
uspto-grants-2011_08
Patent number
US07998983B2

Reaction notes

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