2-Bromopyridine → HCID 20095501, compound

HRID 1770122Notes

Reaction equation

HRID 1770122 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]=O>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 70992Methyl 1H-indole-2-carboxylate

Product 1

HCID 20095501HCID 20095501, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Procedure

A suspension of methyl 1H-indole-2-carboxylate (5.04 g), 2-bromopyridine (3.3 ml), potassium carbonate (7.9 g) and copper (II) oxide (3.9 g) in dry pyridine (80 ml) was heated under reflux for 48 hours. The solvent was removed in vacuo and dichloromethane added to the residue. After filtration the solvent was removed once again in vacuo and the resultant brown oil purified by column chromatography on silica eluting with diethyl ether in petroleum ether (bp 40°-60° C.). Methyl 1-(2-pyridyl)-1H-indole-2-carboxylate was obtained as a white solid: yield 4.74 g (65%). NMR (CDCl3) 3.7 (3H,s,CH3), 7.46 (8H,m,Ar--H), 8.60 (1H,m,Ar--H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customThe solvent was removed in vacuo and dichloromethane
  4. additionadded to the residue
  5. filtrationAfter filtration the solvent
  6. customwas removed once again in vacuo
  7. customthe resultant brown oil purified by column chromatography on silica eluting with diethyl ether in petroleum ether (bp 40°-60° C.)

Sources & evidence

ORD record
ord-0e61defd23e4400684d4d72028f7a693
Source dataset
uspto-grants-1995_01
Patent number
US05385919

Reaction notes

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