Water → HCID 14071978, compound

HRID 1988975Notes

Reaction equation

HRID 1988975 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.O>CN1C(=O)CCC1>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([O:3][C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[CH:6]=[CH:7][NH:8]3)=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 754211H-indol-4-olHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 14071978HCID 14071978, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

NaH (1.1 equivalents) is added to a solution of 4-hydroxyindole (1.0 equivalent) in NMP. The resulting mixture is stirred for 2 hours at room temperature. 2-Chloro-5-nitropyridine (1.1 equivalents) is added and the solution is heated to 100° C. for 2 hours. The solution is cooled and poured into water. The aqueous layer is extracted with EtOAc three times. The organic layers are combined and concentrated to yield the title compound.

Workup

  1. temperaturethe solution is heated to 100° C. for 2 hours
  2. temperatureThe solution is cooled
  3. extractionThe aqueous layer is extracted with EtOAc three times
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a027ae275524e3293193f3c565c2337
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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