Potassium Carbonate → HCID 18796526, compound

HRID 376253Notes

Reaction equation

HRID 376253 reaction equation
CC([O-])(C)C.[K+].Br[CH2:8][CH2:9][CH2:10][OH:11].[N+:12]([C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][NH:21]2)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[OH:11][CH2:10][CH2:9][CH2:8][N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:23]=2)[CH:19]=[CH:20]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 785026-Nitro-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 18796526HCID 18796526, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

0.13 mol of potassium tert-butylate and 0.13 mol of 3-bromopropanol are added to a solution of 0.11 mol of 6-nitroindole in 400 ml of dimethylformamide. The reaction mixture is heated at 80° C. for 3 hours. After cooling, 300 ml of a 10% potassium carbonate solution are added, and the mixture is diluted with ethyl acetate. After decanting, the aqueous phase is extracted with dichloromethane, and the combined organic phases are then concentrated and purified by chromatography on silica gel to yield the expected product.

Workup

  1. temperatureAfter cooling
  2. customAfter decanting
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. concentrationthe combined organic phases are then concentrated
  5. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-25747eb7e1eb4ab2bab610b1c42fb01c
Source dataset
uspto-grants-2000_02
Patent number
US06020336

Reaction notes

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