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

HRID 2205287ノート

反応式

HRID 2205287 の反応式
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

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 117696427HCID 117696427、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
120 °C

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-4ddd3f5ba1bf422c8de5cf9678ef3579
出典データセット
uspto-grants-2016_06
特許番号
US09371282B2

反応ノート

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