Water → Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733741Notes

Reaction equation

HRID 733741 reaction equation
[NH2:1][CH:2]=[C:3]([C:9]1[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:11]=[CH:12][C:13]=1[C:14]([O:16]C)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].CC(C)([O-])C.[Na+].CN(C)C=O.O>C(OCC)(=O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:10]2[C:9]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:2][NH:1][C:14](=[O:16])[C:13]=3[CH:12]=[CH:11]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23676156Sodium t-butoxideHCID 68867423methyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate

Product 1

HCID 57840819Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylateYield 537.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate (2.95 g), sodium tert-butoxide (0.38 g) and dimethylformamide (20 ml) was irradiated with microwaves at 180° C. for 2.5 h. The procedure was repeated five times, the cooled solutions combined, added slowly to iced water then stirred for 25 minutes. A precipitate formed which was dissolved in ethyl acetate and washed with water. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown solid (14.45 g).

Workup

  1. customwas irradiated with microwaves at 180° C. for 2.5 h
  2. customA precipitate formed which
  3. washwashed with water
  4. customThe aqueous layer was separated
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d614094f94f849e98be4e785ceb91649
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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