Potassium Carbonate → HCID 53920417, compound

HRID 485340Notes

Reaction equation

HRID 485340 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]([CH3:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2]1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]=O>[CH2:15]([O:14][C:12]([CH2:11][CH:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:2]=1)[CH3:17])=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 10944294HCID 10944294, compound

Product 1

HCID 53920417HCID 53920417, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

A solution of 2.5 g ethyl 3-(3-indolyl)-butyrate and 1.15 ml of 3-bromopyridine in 25 ml of pyridine is refluxed with 1.25 g of copper oxide and 1.25 g of potassium carbonate for 72 hours, filtered and evaporated to a brown oil which is chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate to yield 3-(3-ethoxycarbonyl-2-propyl)-N-(3-pyridyl)indole; Rf (15% EtOAc, 85% toluene/silica gel)=0.35; IR (CH2Cl2) 1725 cm-1.

Workup

  1. filtrationfiltered
  2. customevaporated to a brown oil which
  3. customis chromatographed on 64 g of silica with 8:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-5bf64bb3f404481f962e716a95ac458e
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

Loading…