Potassium Carbonate → HCID 18005067, compound

HRID 989187Notes

Reaction equation

HRID 989187 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[N+](C1C=CC=CC=1)([O-])=O.O.[Cu]Br>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 225235-Nitroindole

Product 1

HCID 18005067HCID 18005067, compoundYield 86.5%

Reagents, catalysts & solvents 4

HCID 24593copper(I) bromideCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 7416NitrobenzeneSolvent

Procedure

A mixture of 5-nitroindole (0.49 g, 3 mmol), 3-bromopyridine (0.95 g, 6 mmol), copper (I) bromide (60 mg, 0.42 mmol) and potassium carbonate (0.62 g, 4.5 mmol) in pyridine (2 mL) and nitrobenzene (0.6 mL) was heated under reflux for 4 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried and evaporated. The residue was chromatographed on silica gel eluted with ethyl acetate to give the title compound (0.62 g, 86.5%), m.p. 164-5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-46c1a149adc842699bbfbaee80cc538c
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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