Methyl 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate → Methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 2039964Notes

Reaction equation

HRID 2039964 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[NH:10][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 40154011Methyl 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 40152010Methyl 5-amino-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An autoclave is charged with 2.9 g (13.12 mmol) of methyl 5-nitro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (Azasynth), 290 mg of palladium on charcoal 10% and 200 mL of methanol. The reaction mixture is placed under 20 bar of hydrogen, and stirred for 18 h at room temperature. The solution is then filtered on Celite, and the Celite is rinsed with 3×100 mL of hot methanol. The filtrate is evaporated under reduced pressure. 2.38 g of a yellow solid is obtained at a yield of 95%.

Workup

  1. filtrationThe solution is then filtered on Celite
  2. washthe Celite is rinsed with 3×100 mL of hot methanol
  3. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d72e2b87070d4b82b42a77df8fc03ca7
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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