5-Azaindole → 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole

HRID 635923Notes

Reaction equation

HRID 635923 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C>[CH2:13]1[CH:14]2[N:10]([CH2:2][CH:3]=[C:4]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[N:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:5]2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 92205-AzaindoleHCID 31268Pyrrolidine

Product 1

HCID 101309743-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-AzaindoleYield 102.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-azaindole (0.5 g, 4.23 mmol), 1,2,3,5,6,8,8a-heptahydrohydro-7-oxo-indolizine (589 mg, 4.23 mmol) and pyrrolidine (3.0 g, 42.3 mmol) in ethanol (4 mL) were heated to reflux for 6 hrs. The reaction mixture was cooled, filtered, and the collected solid washed with ether to give 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole (0.521 g, 51.6%).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 6 hrs
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washthe collected solid washed with ether

Sources & evidence

ORD record
ord-feab868e0f7f4ebfb97ce1a038163ae6
Source dataset
uspto-grants-2001_02
Patent number
US06191141B1

Reaction notes

Loading…