1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde → HCID 178469527, compound

HRID 402646Notes

Reaction equation

HRID 402646 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]1[O:15][CH2:16][C:17](=[O:24])[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][N:32]=2)[C:27]([CH:34]=O)=[CH:26]1>C(O)C.Cl>[NH:25]1[C:33]2=[N:32][CH:31]=[CH:30][CH:29]=[C:28]2[C:27]([CH:34]=[C:16]2[O:15][C:14]([NH:13][C:7]3[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=3[O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]2=[O:24])=[CH:26]1

Participants

5

Reactant 2

HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708338HCID 86708338, compound

Product 1

HCID 178469527HCID 178469527, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 2-{[2-(2-methoxyethoxy)-4-methylphenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.015 g, 0.045 mmol) which similarly prepared according to the procedure described in the Example 29, First step and 7-azaindole-3-carboxaldehyde (0.0067 g, 0.046 mmol) in ethanol (0.2 mL), 2M hydrochloric acid in ethanol (0.023 mL, 0.045 mmol) was added at ambient temperature. The mixture was refluxed for 4 h. Cooled to ambient temperature, the solvent was removed under reduced pressure. The residue was purified by preparative HPLC to afford the titled compound as solid (0.0090 g, y. 43%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 4 h
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c27bafa3d3b54841926c7dd13453a962
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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