1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde → HCID 178459341, compound

HRID 402676Notes

Reaction equation

HRID 402676 reaction equation
[NH:1]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[C:2]1[C:8]1[O:9][CH2:10][C:11](=[O:19])[C:12]=1[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][N:27]=2)[C:22]([CH:29]=O)=[CH:21]1>CC(O)C>[NH:20]1[C:28]2=[N:27][CH:26]=[CH:25][CH:24]=[C:23]2[C:22]([CH:29]=[C:10]2[O:9][C:8]([C:2]3[NH:1][CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:12]([C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])[C:11]2=[O:19])=[CH:21]1

Participants

4

Reactant 2

HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708381HCID 86708381, compound

Product 1

HCID 178459341HCID 178459341, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of isopropyl 2-azepinyl-4-oxo-4,5-dihydrofuran-3-carboxylate (0.033 g, 0.12 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.019 g, 0.13 mmol) in 2-propanol (1.0 mL), hexamethyleneimine (0.0014 mL, 0.012 mmol) was added at ambient temperature. The mixture was refluxed for 12 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.024 g, y. 49%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 12 days
  3. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-ae02bc7ed3264785b2e6732d23a1715c
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…