Water → HCID 22055705, compound

HRID 1830023Notes

Reaction equation

HRID 1830023 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.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]=[C:11]3[C:7]([CH:8]=[CH:9][NH:10]3)=[CH:6][CH:5]=2)=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 5245086-Hydroxyindole

Product 1

HCID 22055705HCID 22055705, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

NaH (1.1 equivalents) is added to a solution of 6-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 titled 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-3b3303e5426c4125b4f39944b0fe4cb9
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

Loading…