Sodium Hydroxide → HCID 178469528, compound

HRID 402654Notes

Reaction equation

HRID 402654 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[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.[OH-].[Na+]>C(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]([CH3:8])=[CH:7][C:2]=3[OH:1])=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]2=[O:20])=[CH:22]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708343HCID 86708343, compound

Product 1

HCID 178469528HCID 178469528, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent3×

Procedure

To a solution of ethyl 2-[(2-hydroxy-4-methylphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.36 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.061 g, 0.42 mmol) in ethanol (2.5 mL), 2M hydrochloric acid in ethanol (0.56 mL, 1.1 mmol) was added at ambient temperature. The mixture was refluxed for 19 h. Cooled with ice bath, 2M sodium hydroxide solution (0.49 mL, 0.97 mmol) was added dropwise to neutralize, and ethanol (8.0 mL) was added and the mixture was refluxed for 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 (0.027 g, y. 18%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 19 h
  3. temperatureCooled with ice bath
  4. temperaturethe mixture was refluxed for 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-82eaf20c4b4e45c582ebc34250396c98
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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