Sodium Hydroxide → 5-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

HRID 1993598

Reaction equation

HRID 1993598 reaction equation
[OH-].[Na+].CC(C)=O.O.Cl[C:9]1[CH:14]=[C:13]([Cl:15])[N:12]=[CH:11][N:10]=1.[OH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2>CCOC(C)=O.O>[Cl:15][C:13]1[N:12]=[CH:11][N:10]=[C:9]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)[CH:14]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 160545-HydroxyindoleHCID 709434,6-DichloropyrimidineHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 574551565-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of NaOH (720 mg, 18 mmol) and acetone/water 1:1 (72 ml), 4,6-dichloropyrimidine (2.4 g, 18 mmol) and 5-hydroxy-indole (2.68 g, 18 mmol) are added. After stirring for 70 min at 65° C., the brownish solution is cooled to rt and diluted with AcOEt and water. The aqueous layer is separated off and extracted twice with AcOEt. The organic layers are washed with water, saturated Na2CO3 solution, water and brine, dried (Na2SO4) and concentrated. The crude product can be used without further purification: m.p.: 137-138° C.; MS: [M+1]+=246.

Workup

  1. additionare added
  2. temperaturethe brownish solution is cooled to rt
  3. customThe aqueous layer is separated off
  4. extractionextracted twice with AcOEt
  5. washThe organic layers are washed with water, saturated Na2CO3 solution, water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product can be used without further purification

Sources & evidence

ORD record
ord-fda71291314b4954ab91941c4e258e26
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Linked notes

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