Trimethylsilylacetylene → 2-Chloro-6-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]pyridine

HRID 386055ノート

反応式

HRID 386055 の反応式
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[N:5]=1)=[N+:2]=[N-:3].[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[Cl:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N:1]2[CH:16]=[C:15]([Si:12]([CH3:14])([CH3:13])[CH3:11])[N:3]=[N:2]2)[N:5]=1

参加物

7

反応物 3

HCID 66111TrimethylsilylacetyleneHCID 215763792-Azido-6-chloropyridineHCID 23667548Sodium Ascorbate

生成物 1

HCID 595262262-Chloro-6-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]pyridine

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-Azido-6-chloropyridine (500 mg, 3.24 mmol) and trimethylsilylacetylene (545 μL, 3.88 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL) CuSO4.5H2O (40 mg, 0.16 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (128 mg, 0.65 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), and evaporated to a crude residue that was purified by flash chromatography (0-40% 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. customevaporated to a crude residue that
  5. customwas purified by flash chromatography (0-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-2985eda65de548ebbd94a20c94fb2988
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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