Potassium Carbonate → HCID 20270210, compound

HRID 485350Notes

Reaction equation

HRID 485350 reaction equation
[C:1]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2].Br[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]=O>[C:1]([C:6]1[N:7]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 20270210HCID 20270210, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

A solution of 10.0 g of 2-carboethoxyindole and 5 ml of 3-bromopyridine in 50 ml of pyridine is refluxed with 5.0 g of copper oxide and 5.0 g of potassium carbonate for 72 hours. Filtration and evaporation yields an oil which is chromatographed on 110 g of silica with 15% ethyl acetate in toluene to yield 2-carboethoxy-N-(3-pyridyl)indole as an oil; IR (CH2Cl2) 1705 cm-1.

Workup

  1. filtrationFiltration and evaporation
  2. customyields an oil which
  3. customis chromatographed on 110 g of silica with 15% ethyl acetate in toluene

Sources & evidence

ORD record
ord-0d4fca573f7f45d1812317aa5dea166c
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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