Sodium borohydride → HCID 59674980, 화합물

HRID 1010703노트

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HRID 1010703 반응식
[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

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 67313333HCID 67313333, 화합물

생성물 1

HCID 59674980HCID 59674980, 화합물수율 75.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0b98207ad34f483b90e82c4747227acb
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977341B2

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