1,3-dimethyl-1H-pyrrole → HCID 67355881、化合物

HRID 1478892ノート

反応式

HRID 1478892 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][C:18]([CH3:21])=[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[C:18]([CH3:21])=[CH:17]1

参加物

5

反応物 2

HCID 109644171,3-dimethyl-1H-pyrroleHCID 86674845HCID 86674845、化合物

生成物 1

HCID 67355881HCID 67355881、化合物収率 55%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

In a 500 ml round bottom flask, methyl 3-(dimethylamino)-2-((dimethylamino)methyleneamino)acrylate (1A, 12 g, 61 mmol) was dissolved in acetic acid (45 ml) and TFA (15 ml). 1,3-Dimethyl-1H-pyrrole (5.8 g, 61 mmol) was added and the mixture was stirred at room temperature for an hour and then at 110° C. for 4 hours. Volatiles were then evaporated from the reaction mixture, the residue was cooled in an ice bath and 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 a silica column using hexane-EtOAc (0-100%). Desired product methyl 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1J, 6.8 g, 55%) was obtained.

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 a silica column

出典と根拠

ORDレコード
ord-d331f50568a647939281cd8e4687cb73
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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