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

HRID 733717Notes

Reaction equation

HRID 733717 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6]=1[C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][NH2:13])=O.CC(C)([O-])C.[Na+]>CN(C)C=O>[CH3:17][O:16][C:14]([C:11]1[C:6]2[N:7]([CH3:10])[CH:8]=[CH:9][C:5]=2[C:3](=[O:2])[NH:13][CH:12]=1)=[O:15]

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 39.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-amino-1-methoxycarbonyl-vinyl)-1-methyl-1H-pyrrole-3-carboxylic acid methyl ester (3.3 g), sodium tert-butoxide (0.267 g) and dimethylformamide (22 ml) was split equally between 2×20 ml sealed vessels and irradiated with microwaves at 160° C. for 5 minutes. The cooled solutions were combined and added slowly to ice water and stirred for 10 minutes. A precipitate formed which was filtered off and dried to yield the title compound as a white solid (1.12 g). The aqueous filtrate was extracted three times with ethyl acetate and the combined organics were washed with saturated brine solution. The dried (Na2SO4) organic layer was evaporated to yield a yellow oil which was triturated with warm isopropyl alcohol to yield the title compound as a white solid (0.66 g). Total product weight (1.78 g).

Workup

  1. customwas split equally between 2×20 ml
  2. customsealed vessels
  3. customirradiated with microwaves at 160° C. for 5 minutes
  4. additionadded slowly to ice water
  5. customA precipitate formed which
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-712286c3c876499db036b3dc101420f1
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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