Sodium Hydroxide → HCID 178469598, compound

HRID 402644Notes

Reaction equation

HRID 402644 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][O:11][CH3:12])[CH:5]=[CH:4][C:3]=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.[OH-].[Na+]>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:3]3[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:7][C:2]=3[F:1])=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]2=[O:24])=[CH:26]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708335HCID 86708335, compound

Product 1

HCID 178469598HCID 178469598, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent3×

Procedure

To a solution of ethyl 2-{[2-fluoro-4-(2-methoxyethoxy)phenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.011 g, 0.032 mmol) which similarly prepared according to the procedure described in the Example 29, First step and 7-azaindole-3-carboxaldehyde (0.0045 g, 0.031 mmol) in ethanol (0.2 mL), 2M hydrochloric acid in ethanol (0.016 mL, 0.032 mmol) was added at ambient temperature. The mixture was refluxed for 4 h. Cooled with ice bath, 2M sodium hydroxide solution (0.015 mL, 0.029 mmol) was added dropwise to neutralize, and ethanol (1.5 mL) was added. The mixture was refluxed for further 30 min. The precipitate was collected by filtration, washed with hot ethanol. The solid was washed with hexane then dried to afford the titled compound as solid (0.0051 g, y. 32%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 4 h
  3. temperatureCooled with ice bath
  4. temperatureThe mixture was refluxed for further 30 min
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with hot ethanol
  7. washThe solid was washed with hexane
  8. customthen dried

Sources & evidence

ORD record
ord-a2876bd7c6ea493ea333631bdac0ae5d
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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