Water → Ethyl pyrazolo(1,5-a)pyridine-3-carboxylate

HRID 1500753노트

반응식

HRID 1500753 반응식
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][CH3:3].[I-].[NH2:9][N+:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[N:9]1[N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7749Ethyl PropionateHCID 11430Potassium CarbonateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)

생성물 1

HCID 2795464Ethyl pyrazolo(1,5-a)pyridine-3-carboxylate수율 50.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl propionate (50.2 mL, 49.54 mmol) and 1-aminopyridinium iodide (10.0 g, 45 mmol) were added to a suspension of potassium carbonate (8.71 g, 63.02 mmol) in N,N′-dimethylformamide (100 mL) and the resulting mixture was stirred at room temperature for 2 h before being poured into 100 mL of water. Ethyl acetate was then added and the aqueous layer was separated and washed with ethyl acetate (×2). The combined organic layers were dried over magnesium sulphate, filtered and evaporated. The crude product was purified by flash chromatography (hexanes to 4:1 hexanes/ethyl acetate) to give the title compound (4.30 g, 50%) as an orange solid.

후처리

  1. customthe aqueous layer was separated
  2. washwashed with ethyl acetate (×2)
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (hexanes to 4:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-4595d3b4cce34da385b5d3d0168d3b06
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206183B2

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