Ethanol → HCID 178469557, compound

HRID 402630Notes

Reaction equation

HRID 402630 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[O:11][CH2:12][C:13](=[O:20])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][N:28]=2)[C:23]([CH:30]=O)=[CH:22]1.C(O)C.[OH-].[Na+]>CC(O)C.Cl>[NH:21]1[C:29]2=[N:28][CH:27]=[CH:26][CH:25]=[C:24]2[C:23]([CH:30]=[C:12]2[O:11][C:10]([NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]2=[O:20])=[CH:22]1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708324HCID 86708324, compound

Product 1

HCID 178469557HCID 178469557, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 2-[(2,4-difluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.15 g, 0.54 mmol) which similarly prepared according to the procedure described in the Example 2, First step and 7-azaindole-3-carboxaldehyde (0.074 g, 0.50 mmol) in 2-propanol (2.5 mL), 2M hydrochloric acid in ethanol (0.25 mL, 0.50 mmol) was added at ambient temperature then refluxed for 24 h. Cooled with ice bath, aqueous 2M sodium hydroxide solution (0.024 mL, 0.048 mmol) was added dropwise to neutralize and the mixture was refluxed for 1 h. The precipitate was collected by filtration, washed with ethanol and hexane then dried to afford the titled compound as solid (0.14 g, y. 69%).

Workup

  1. additionwas added at ambient temperature
  2. temperaturethen refluxed for 24 h
  3. temperatureCooled with ice bath
  4. temperaturethe mixture was refluxed for 1 h
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethanol and hexane
  7. customthen dried

Sources & evidence

ORD record
ord-53558b69c7484a199f4404ad38b29e7e
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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