Ethanol → HCID 178469559, compound

HRID 402631Notes

Reaction equation

HRID 402631 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:11][CH2:12][C:13](=[O:20])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[F:8].[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:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)=[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 702Ethanol2×HCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708326HCID 86708326, compound

Product 1

HCID 178469559HCID 178469559, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of ethyl 2-[(3,4-difluorophenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.084 g, 0.30 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.041 g, 0.28 mmol) in 2-propanol (2.0 mL), 2M hydrochloric acid in ethanol (0.14 mL, 0.28 mmol) was added at ambient temperature. The mixture was refluxed for 18 h. Cooled with ice bath, aqueous 2M sodium hydroxide solution (0.13 mL, 0.26 mmol) was added dropwise to neutralize, ethanol (5.0 mL) was added and the mixture was refluxed for 1.5 h. 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 (0.051 g, y. 44%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 18 h
  3. temperatureCooled with ice bath
  4. temperaturethe mixture was refluxed for 1.5 h
  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-38ece163b8f44ae6b2545a5952b3cdb2
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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