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

HRID 2060604

반응식

HRID 2060604 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 61499Cupric sulfate monohydrate촉매HCID 962Water용매3회HCID 6386tert-Butanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c32ea3739e9a4fdea2d8d0cdf70cbe0f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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