Sodium Hydroxide → HCID 178469596, compound

HRID 402645Notes

Reaction equation

HRID 402645 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[O:14][CH2:15][C:16](=[O:23])[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][N:31]=2)[C:26]([CH:33]=O)=[CH:25]1.[OH-].[Na+]>C(O)C.Cl>[NH:24]1[C:32]2=[N:31][CH:30]=[CH:29][CH:28]=[C:27]2[C:26]([CH:33]=[C:15]2[O:14][C:13]([NH:12][C:3]3[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][OH:11])=[CH:7][C:2]=3[F:1])=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]2=[O:23])=[CH:25]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708337HCID 86708337, compound

Product 1

HCID 178469596HCID 178469596, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent3×

Procedure

To a solution of ethyl 2-{[2-fluoro-4-(2-hydroxyethoxy)phenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.017 g, 0.052 mmol) which similarly prepared according to the procedure described in the Example 29, First step and 7-azaindole-3-carboxaldehyde (0.0075 g, 0.051 mmol) in ethanol (0.2 mL), 2M hydrochloric acid in ethanol (0.052 mL, 0.10 mmol) was added at ambient temperature. The mixture was refluxed for 8.5 h. Cooled with ice bath, 2M sodium hydroxide solution (0.047 mL, 0.094 mmol) was added dropwise to neutralize, and ethanol (0.5 mL) was added and refluxed for further 16 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 (0.014 g, y. 59%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 8.5 h
  3. temperatureCooled with ice bath
  4. temperaturerefluxed for further 16 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-f5275481134541fd9f616153ffcd9c89
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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