2,5-Hexanedione → 5-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-indole

HRID 1419170Notes

Reaction equation

HRID 1419170 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]([CH2:15][C:16](=O)[CH3:17])[C:12]([CH3:14])=O>C1(C)C=CC=CC=1>[CH3:17][C:16]1[N:1]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[C:12]([CH3:14])=[CH:11][CH:15]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 788675-Aminoindole

Product 1

HCID 100818535-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-indoleYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-aminoindole (1.32 g, 10.0 mmol), acetonylacetone (4.0 mL, 34 mmol, 3.4 eq) and toluene (25 mL) was heated at reflux under nitrogen using a Dean-Stark trap for 24 hours. The reaction was cooled and then poured through a silica gel (approximately 200 g) filter followed by 10% ether in hexanes to afford the title compound (1.52 g, 72%) as an off-white, crystalline solid: Rf =0.75 in diethyl ether; 13C NMR (CDCl3) δ 135.0, 131.4, 129.5, 128.1, 125.6, 122.4, 120.3, 111.3, 105.0, 103.0, 13.2. Anal. calcd for C14H14N2 ; C, 79.97; H, 6.71; N, 13.32. Found: C, 79.72; H, 6.75; N, 13.13.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen using a Dean-Stark trap for 24 hours
  3. temperatureThe reaction was cooled
  4. additionpoured through a silica gel (approximately 200 g)
  5. filtrationfilter

Sources & evidence

ORD record
ord-316b8026e98244e0a0c5e0c7c7040bf6
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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