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 1793851ノート

反応式

HRID 1793851 の反応式
[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

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 11334553HCID 11334553、化合物HCID 178418936HCID 178418936、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e8c06cb7a30414e9ca0ba08fcea7f14
出典データセット
uspto-grants-2006_04
特許番号
US07022705B2

反応ノート

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