2,5-Hexanedione → HCID 11396043, compound

HRID 916199Notes

Reaction equation

HRID 916199 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])C.[CH2:29]([CH2:33][C:34](=O)[CH3:35])[C:30]([CH3:32])=O.O.[OH-].[Li+]>C1(C)C=CC=CC=1>[CH3:35][C:34]1[N:28]([C:25]2[CH:24]=[CH:23][C:22]([CH2:21][N:7]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[C:6]3[C:4]([OH:3])=[O:5])=[CH:27][CH:26]=2)[C:30]([CH3:32])=[CH:29][CH:33]=1

Participants

5

Reactant 3

HCID 80352,5-HexanedioneHCID 168937Lithium hydroxide, monohydrateHCID 694333051h-Indole-2-carboxylic acid,1-[(4-aminophenyl)methyl]-3-phenyl-,ethyl ester

Product 1

HCID 11396043HCID 11396043, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-amino-benzyl)-3-phenyl-1H-indolecarboxylic acid ethyl ester (0.20 g, 0.54 mmol), acetonylacetone (0.16 mL, 1.35 mmol), and toluene (15 mL) was heated at reflux under nitrogen using a Dean-Stark trap for 6 h. The reaction was cooled and concentrated. The residue was re-dissolved in 10 mL of 2:1:1 THF/MeOH/water. Lithium hydroxide monohydrate (0.09 g, 2.1 mmol) was added and the mixture was stirred at room temperature overnight. Most of the organic solvents was removed and the reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and purified by HPLC to afford the title compound (0.027 g, 6%) as a brown solid: 1H NMR (DMSO-d6) δ 1.91 (s, 6H), 5.75 (s, 2H), 7.01-7.30 (m, 6H), 7.32-7.38 (m, 2H), 7.40-7.50 (m, 6H), 7.68 (d, J=8.54 Hz, 1H), 12.80 (br s, 1H); MS (ESI) m/z 421 (MH+); MS (ESI) m/z 419 ([M−H]−); HRMS calcd for C28H26N2O2: 421.1905; found (ESI+): 421.1915.

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. dissolutionThe residue was re-dissolved in 10 mL of 2:1:1 THF/MeOH/water
  6. customMost of the organic solvents was removed
  7. customthe solid was collected
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-3610a152fdd246c198cdc11302445bb6
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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