Dimethyl Sulfoxide → HCID 66860822, compound

HRID 388186Notes

Reaction equation

HRID 388186 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:14][C:13]=2[CH:12]=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>[Cu].C(Cl)(Cl)Cl>[Br:8][C:4]1[CH:3]=[C:2]([N:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:21]3[CH:9]=[N:10][CH:11]=[CH:12][C:13]2=3)[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 130802gamma-Carboline

Product 1

HCID 66860822HCID 66860822, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

Another reaction vessel was charged with 17.2 ml of 1,3-dibromobenzene, 6.0 g of 5H-pyrido[4,3-b]indole, 1.1 g of copper powder, 9.9 g of potassium carbonate, and 0.6 ml of dimethyl sulfoxide, followed by heating and stirring at 180° C. for 4 hours. After cooling to room temperature, 50 ml of chloroform was added thereto, the insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: silica gel, eluent: hexane/chloroform) to obtain 7.1 g (yield 62%) of 5-(3-bromophenyl)-5H-pyrido[4,3-b]indole as a white powder.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling to room temperature
  3. customthe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto obtain a crude product
  6. customThe crude product was purified by column chromatography (carrier: silica gel, eluent: hexane/chloroform)

Sources & evidence

ORD record
ord-ebb83eaeba70405ca68db5f5be34185b
Source dataset
uspto-grants-2013_02
Patent number
US08377573B2

Reaction notes

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