Potassium Carbonate → 1-Methyl-1H-pyrazolo[4,3-b]pyridine

HRID 2205287노트

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HRID 2205287 반응식
Br[C:2]1[C:3]([CH:8]=[N:9][NH:10][CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cl-].[NH4+].C(OCC)(=O)C.[Cu]I>[CH3:11][N:10]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[N:9]1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 117696427HCID 117696427, 화합물

생성물 1

HCID 569722961-Methyl-1H-pyrazolo[4,3-b]pyridine수율 16.4%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매HCID 25517Ammonium Chloride용매

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온도
120 °C

실험 절차

N-[1-(3-Bromo-pyridin-2-yl)-methylidene]-N′-methyl-hydrazine (5.7 g, 26.63 mmol), copper (I) iodide (507 mg, 2.66 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (76 mg, 0.533 mmol) and potassium carbonate (7.36 g, 53.25 mmol) are suspended in 1-methyl-2-pyrrolidinone (20 mL) and heated at 120° C. for 3 h. The mixture is diluted with saturated ammonium chloride solution and ethyl acetate. The resulting emulsion is filtered, the phases separated and the organic phase washed with brine, dried and volatiles evaporated under reduced pressure. The residue is redissolved in ethyl ether, washed with brine and the solvent removed. The residue is purified by flash chromatography (0-60% EtOAc in cyclohexane) to give 1-methyl-1H-pyrazolo[4,3-b]pyridine (580 mg, content 85%, 14%)

후처리

  1. filtrationThe resulting emulsion is filtered
  2. customthe phases separated
  3. washthe organic phase washed with brine
  4. customdried
  5. customvolatiles evaporated under reduced pressure
  6. dissolutionThe residue is redissolved in ethyl ether
  7. washwashed with brine
  8. customthe solvent removed
  9. customThe residue is purified by flash chromatography (0-60% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-4ddd3f5ba1bf422c8de5cf9678ef3579
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371282B2

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