Trimethylsilylmethyl Azide → HCID 59525895、化合物

HRID 386067

反応式

HRID 386067 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]#[CH:10])[N:3]=1.[CH3:12][Si:13]([CH2:16][N:17]=[N+:18]=[N-:19])([CH3:15])[CH3:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]2[N:19]=[N:18][N:17]([CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[CH:10]=2)[N:3]=1

参加物

7

反応物 3

HCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 595259492-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine

生成物 1

HCID 59525895HCID 59525895、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒3 回HCID 6386tert-Butanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

2-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine (520 mg, 2.43 mmol) and trimethylsilylmethyl azide (377 mg, 2.92 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL). CuSO4.5H2O (30 mg, 0.12 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (96 mg, 0.49 mmol) in water (1.0 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to a brown residue that was purified by flash chromatography (0-30% EtOAc/hexanes) to afford the title compound as a colorless solid.

後処理

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a brown residue that
  6. customwas purified by flash chromatography (0-30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-91ced9ba13bd4ff0b33a986cbd7427cc
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

関連ノート

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