Sodium t-butoxide → Methyl 4,5-dihydro-1-methyl-4-oxo-1H-pyrrolo[3,2-C]pyridine-7-carboxylate

HRID 733690Notes

Reaction equation

HRID 733690 reaction equation
[NH2:1][CH:2]=[C:3]([C:8]1[N:9]([CH3:17])[CH:10]=[CH:11][C:12]=1[C:13](OC)=[O:14])[C:4]([O:6][CH3:7])=[O:5].CC(C)([O-])C.[Na+]>CN(C)C=O>[CH3:17][N:9]1[C:8]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:2][NH:1][C:13](=[O:14])[C:12]=2[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 68866598methyl 2-{2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 44475352Methyl 4,5-dihydro-1-methyl-4-oxo-1H-pyrrolo[3,2-C]pyridine-7-carboxylateYield 987.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-{2-amino-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate (2 g) and sodium t-butoxide (160 mg) in dimethylformamide (18 ml) was irradiated within a microwave reactor at 160° C. for 20 minutes. The reaction was repeated 28 times. The reaction mixtures were combined (56.4 g) and after cooling a precipitate formed which was filtered, washed with water and dried in vacuo to yield the title compound (17.1 g).

Workup

  1. customwas irradiated within a microwave reactor at 160° C. for 20 minutes
  2. customThe reaction mixtures
  3. temperatureafter cooling a precipitate
  4. customformed which
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-702b650eb40043e0b3ea0d7a55ee5ec9
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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