Trifluoroacetic acid → HCID 89925499, compound

HRID 922470Notes

Reaction equation

HRID 922470 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.CN(C)[CH:13]=[C:14]([N:20]=[CH:21]N(C)C)[C:15]([O:17][CH2:18][CH3:19])=[O:16].FC(F)(F)C(O)=O>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:20]=[CH:21][C:9]=2[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 43394783HCID 43394783, compoundHCID 54287818HCID 54287818, compound

Product 1

HCID 89925499HCID 89925499, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(3-methoxypropyl)-1H-pyrrole (3.92 g), ethyl 3-dimethylamino-2-(dimethylaminomethyleneamino)acrylate (7.20 g) (ref. Liebigs Ann. Chem. 1980, 344-357) and trifluoroacetic acid (8.33 mL) in acetic acid (32 mL) was stirred at room temperature for 18 hours, and then heated to reflux for 3 hours. After cooling, the reaction solution was concentrated under reduced pressure. To the resulting residue was added aqueous saturated sodium hydrogen carbonate solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1→AcOEt) to give ethyl 1-(3-methoxypropyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate [REx(105.2)] (4.79 g) as a brown oil.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. additionTo the resulting residue was added aqueous saturated sodium hydrogen carbonate solution under ice-
  6. temperaturecooling
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated saline
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1→AcOEt)

Sources & evidence

ORD record
ord-84fd0588b7f74757bc33c5eade431108
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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