Methyl propiolate → Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-4-carboxylate

HRID 2060604

反応式

HRID 2060604 の反応式
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[N:12]=1)=[N+:8]=[N-:9].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Cu+2].O>[Br:17][C:13]1[N:12]=[C:11]([CH2:10][N:7]2[CH:3]=[C:2]([C:1]([O:5][CH3:6])=[O:4])[N:9]=[N:8]2)[CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 3

HCID 13536Methyl propiolateHCID 23667548Sodium AscorbateHCID 453574032-(Azidomethyl)-6-bromopyridine

生成物 1

HCID 58335253Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-4-carboxylate

試薬・触媒・溶媒 4

HCID 61499Cupric sulfate monohydrate触媒HCID 962Water溶媒3 回HCID 6386tert-Butanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Methyl propiolate (641 μL, 7.63 mmol) and 2-(azidomethyl)-6-bromopyridine (1.25 g, 5.87 mmol) were combined in t-BuOH (9.0 mL) and water (5.0 mL). A solution of CuSO4.H2O (73 mg, 0.29 mmol) in water (2.0 mL) was added, followed by sodium ascorbate (232 mg, 1.17 mmol) in water (2.0 mL). The reaction was stirred at room temperature for 18 h, during which time it became a yellow suspension. The suspension was diluted with saturated NaHCO3 and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to dryness. The crude solid was purified by flash chromatography (40-100% ethyl acetate/hexanes) to afford the title compound as a colorless solid. LRMS (APCI) calc'd for C10H10BrN4O2 [M+H]+: 297, Found: 297.

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe crude solid was purified by flash chromatography (40-100% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-c32ea3739e9a4fdea2d8d0cdf70cbe0f
出典データセット
uspto-grants-2012_10
特許番号
US08278335B2

関連ノート

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