2,5-Hexanedione → ethyl 1-benzyl-5-(2,5-dimethyl-1H-pyrrol-1-yl)-3-phenyl-1H-indole-2-carboxylate

HRID 915345Notes

Reaction equation

HRID 915345 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:29]([CH2:33][C:34](=O)[CH3:35])[C:30]([CH3:32])=O>C1(C)C=CC=CC=1>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([N:1]3[C:34]([CH3:35])=[CH:33][CH:29]=[C:30]3[CH3:32])=[CH:10][CH:9]=2)[C:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:6]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 69229300ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69340875ethyl 1-benzyl-5-(2,5-dimethyl-1H-pyrrol-1-yl)-3-phenyl-1H-indole-2-carboxylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate (0.93 g, 2.5 mmol), acetonylacetone (2.5 mL, 21.3 mmol), and toluene (25 mL) was heated at reflux under nitrogen using a Dean-Stark trap for 6 h. The reaction was cooled and concentrated. The residue was then purified by flash silica gel chromatography (hexanes/ethyl acetate 4/1) to afford 1.0 g (89%) of ethyl 1-benzyl-5-(2,5-dimethyl-1H-pyrrol-1-yl)-3-phenyl-1H-indole-2-carboxylate as a white solid: 1H NMR (CDCl3) δ 0.99 (t, J=7.1 Hz, 3 H), 2.00 (s, 6 H), 4.15 (q, J=7.1 Hz, 2 H), 5.83 (s, 2 H), 5.86 (s, 2 H), 7.10-7.51 (m, 13 H); MS (ESI) m/z (MH+) 449; Anal. calcd for C30H28N2O2.0.25 H2O: C, 79.53; H, 6.34; N, 6.18. Found: C, 79.67; H, 6.40; N, 5.91.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen using a Dean-Stark trap for 6 h
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customThe residue was then purified by flash silica gel chromatography (hexanes/ethyl acetate 4/1)

Sources & evidence

ORD record
ord-8cae1cdc60a945a2982d3d4fdf6a6eeb
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

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