Potassium Carbonate → HCID 18005067, compound

HRID 1603775Notes

Reaction equation

HRID 1603775 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 tide compound (0.62 g, 86.5%), mp. 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-76dce4ee258c4b6d967cd266075203c3
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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