1-Methylpyrrole → HCID 86674844、化合物

HRID 1478891ノート

反応式

HRID 1478891 の反応式
CN(C)[CH:3]=[C:4]([N:9]=[CH:10]N(C)C)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][N:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>C(O)(=O)C.C(O)(C(F)(F)F)=O>[CH3:15][N:16]1[C:20]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[N:9]=[CH:10][C:19]=2[CH:18]=[CH:17]1

参加物

5

反応物 2

HCID 73041-MethylpyrroleHCID 86674845HCID 86674845、化合物

生成物 1

HCID 86674844HCID 86674844、化合物収率 38%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
110 °C

実験手順

In a 500 ml round bottom flask, methyl 3-(dimethylamino)-2-((dimethylamino)methyleneamino)acrylate (1A, 24 g, 120 mmol) was dissolved in acetic acid (60 ml) and TFA (20 ml). 1-Methyl-1H-pyrrole (10.56 ml, 119 mmol) was added. The mixture was stirred at room temperature for an hour and at 110° C. for 4 hours until completion of the reaction. Volatiles were then evaporated from the reaction mixture, the residue was cooled in an ice bath. Ice cold saturated K2CO3 solution (200 ml) was slowly added to it. The mixture was extracted with EtOAc (3×250 ml). Combined organic layers were then washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified on silica column using hexane-EtOAc (0-100%). Desired product methyl 1-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1B, 8.5 g, 38%) was obtained as a thick brown oil.

後処理

  1. customVolatiles were then evaporated from the reaction mixture
  2. temperaturethe residue was cooled in an ice bath
  3. additionIce cold saturated K2CO3 solution (200 ml) was slowly added to it
  4. extractionThe mixture was extracted with EtOAc (3×250 ml)
  5. washCombined organic layers were then washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified on silica column

出典と根拠

ORDレコード
ord-e05255132fd141e6abc0f354c80fd1ef
出典データセット
uspto-grants-2016_08
特許番号
US09403819B2

反応ノート

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