Potassium Carbonate → 2-(1-Hydroxy-1-methyl-ethyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

HRID 549390노트

반응식

HRID 549390 반응식
[I-].[NH2:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][C:18](=[O:25])[C:19]#[C:20][C:21]([OH:24])([CH3:23])[CH3:22])[CH3:16]>CN(C)C=O>[CH2:15]([O:17][C:18]([C:19]1[C:20]([C:21]([OH:24])([CH3:23])[CH3:22])=[N:2][N:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=12)=[O:25])[CH3:16]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 112289264-Hydroxy-4-methyl-pent-2-ynoic acid ethyl ester

생성물 1

HCID 578992642-(1-Hydroxy-1-methyl-ethyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester수율 77.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of 1-amino-pyridinium iodide (0.343 g, 1.54 mmol) and potassium carbonate (0.278 g, 2.01 mmol) in 2 mL N,N-dimethylformamide was added 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester (0.262 g, 1.70 mmol) in 1 mL N,N-dimethylformamide dropwise. The mixture was stirred at room temperature for 24 h under nitrogen atmosphere, poured on to ice and filtered, and the solid was washed with water to provide the crude product as a brown solid. The filtrate was extracted with ethyl acetate and the previously filtered solid was combined with the organic extracts, which was dried over magnesium sulfate, filtered and concentrated in vacuo and the residue was purified via silica gel column chromatography (0-50% ethyl acetate in heptane) to obtain the product as a yellow solid (0.296 g, 1.19 mmol, 77% yield).

후처리

  1. additionpoured on to ice
  2. filtrationfiltered
  3. washthe solid was washed with water
  4. customto provide the crude product as a brown solid
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified via silica gel column chromatography (0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-47993745a344495b8242501bfb3d00f0
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943652B2

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