Sodium hydride → (5RS)-3-(3-Fluoro-4-(1,2,3-triazol-1-yl)phenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole

HRID 1793851노트

반응식

HRID 1793851 반응식
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[N:4]1.[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH2:20][CH:19]([CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[N:23]3)[O:18][N:17]=2)[CH:12]=[CH:13][C:14]=1F>CN(C)C=O>[F:8][C:9]1[CH:10]=[C:11]([C:16]2[CH2:20][CH:19]([CH2:21][N:22]3[CH:26]=[CH:25][N:24]=[N:23]3)[O:18][N:17]=2)[CH:12]=[CH:13][C:14]=1[N:3]1[CH:7]=[CH:6][N:5]=[N:4]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 11334553HCID 11334553, 화합물HCID 178418936HCID 178418936, 화합물

생성물 1

HCID 9879819(5RS)-3-(3-Fluoro-4-(1,2,3-triazol-1-yl)phenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole수율 3.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A slurry of sodium hydride (60% in oil, 44 mg, 1.1 mM) in anhydrous N,N-dimethylformamide (1 ml) was stirred under an atmosphere of nitrogen and treated dropwise with a solution of 1,2,3-triazole (76 mg, 1.1 mM) in anhydrous N,N-dimethylformamide (1 ml) at 0°. The mixture was allowed to warm to ambient temperature over 20 minutes, then a solution of (5RS)-3-(3,4-difluorophenyl)-5-(1,2,3-triazol-1-yl-methyl)-4,5-dihydroisoxazole (264 mg, 1 mM) in anhydrous N,N-dimethylformamide (2 ml) added, and the mixture stirred at 70° for 16 hours. After cooling, the mixture was partitioned between aqueous sodium bicarbonate solution (40 ml) and ethyl acetate (40 ml), and the organic extract washed with water (40 ml) and brine (40 ml). After drying (magnesium sulfate) and evaporation, the crude product was chromatographed on a 20 g silica Mega Bond Elut® column, eluting with ethyl acetate. Relevant fractions were combined to give the desired product (12 mg).

후처리

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between aqueous sodium bicarbonate solution (40 ml) and ethyl acetate (40 ml)
  3. extractionthe organic extract
  4. washwashed with water (40 ml) and brine (40 ml)
  5. customAfter drying
  6. custom(magnesium sulfate) and evaporation
  7. customthe crude product was chromatographed on a 20 g silica Mega Bond Elut® column
  8. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-1e8c06cb7a30414e9ca0ba08fcea7f14
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022705B2

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