10524-65-9 → HCID 67355881, compound

HRID 2405079Notes

Reaction equation

HRID 2405079 reaction equation
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

Participants

5

Reactant 2

HCID 1096441710524-65-9HCID 86674845HCID 86674845, compound

Product 1

HCID 67355881HCID 67355881, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b87f9432d7cf43f0a99696dc09816efd
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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