benzyl 4-[(methoxycarbonyl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate → methyl 1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate

HRID 2201800Notes

Reaction equation

HRID 2201800 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[C:11]2[CH:12]=[CH:13][N:14](C(OCC3C=CC=CC=3)=O)[C:10]=2[CH:9]=[CH:8][N:7]=1)=[O:4]>C(O)C.[Pd]>[NH:14]1[C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[C:11]=2[CH:12]=[CH:13]1

Participants

4

Reactant 1

HCID 71061748benzyl 4-[(methoxycarbonyl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 86720632methyl 1H-pyrrolo[3,2-c]pyridin-4-ylcarbamateYield 90.75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of benzyl 4-[(methoxycarbonyl)amino]-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (264 mg, 0.82 mmol, Step a) in ethanol (10 mL) was added catalytic amount of palladium on carbon (10% wet). The reaction mixture was stirred under an atmosphere of hydrogen gas (atmospheric pressure) for 1 hour. The reaction mixture was filtered over celite and the residue washed with ethanol. The filtrate was concentrated to yield methyl 1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate as a white powder (141 mg, 90.75%).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washthe residue washed with ethanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-06ae6cdd4a6c4031957e688d6debac56
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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