Acetic acid, azido-, ethyl ester → ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

HRID 386062

反応式

HRID 386062 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[N:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:11]=[N-:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:12]=[N:11]1)[CH3:18]

参加物

7

反応物 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 129705322-Bromo-6-ethynylpyridineHCID 23667548Sodium Ascorbate

生成物 1

HCID 59525977ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

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-ethynylpyridine (Example 465, Step 1) (350 mg, 1.92 mmol) and ethyl azidoacetate (1.08 ml, 1.92 mmol) were combined in t-BuOH (4.0 mL) and water (2.0 mL). CuSO4.5H2O (24 mg, 0.096 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (76 mg, 0.39 mmol) in water (1.0 mL). The reaction was stirred at room temperature for 5 h, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to a yellow 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 yellow residue that
  6. customwas purified by flash chromatography (0-30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-c07ac8fa129843fba3c3213505dc47fb
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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