Ammonia → 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 550897Notes

Reaction equation

HRID 550897 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([O:19]C)=O)=[CH:4][CH:3]=1.[NH3:21]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([NH2:21])=[O:19])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 57445355methyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 574453543-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 260 mg of methyl 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate in 30 mL of a 7N solution of ammonia in methanol are added 5 mL of 22% aqueous ammonia solution. The reaction mixture is then stirred for 20 hours in an autoclave at 80° C. (12.6 bar) and then concentrated under reduced pressure. The residue obtained is chromatographed on a column of silica (eluent: 9/1 dichloromethane/methanol by volume). The fractions containing the expected product are concentrated under reduced pressure. 140 mg of 3-(4-aminophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide are obtained in the form of a pale yellow solid, the characteristics of which are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. customis chromatographed on a column of silica (eluent: 9/1 dichloromethane/methanol by volume)
  4. additionThe fractions containing the expected product
  5. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5f35de89aad44f0a15c75e32a8c37ac
Source dataset
uspto-grants-2011_05
Patent number
US07947706B2

Reaction notes

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