p-Toluenesulfonic acid → HCID 70562744, compound

HRID 1477850Notes

Reaction equation

HRID 1477850 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([CH2:16][CH3:17])[C:12]([O:14][CH3:15])=[O:13].[CH3:25][C:26](=O)[CH2:27][CH2:28][C:29](=O)[CH3:30].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([N:1]4[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]4[CH3:25])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)([CH2:16][CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 70565237HCID 70565237, compound

Product 1

HCID 70562744HCID 70562744, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-(4-amino-1H-indol-1-yl)-2-(4-chlorophenyl)butanoate (140 mg), hexane-2,5-dione (166 mg) and 4-methylbenzenesulfonic acid (3 mg) in toluene (5 mL) was stirred under reflux for 30 min. Concentrated, the residue was purified by chromatography on silica gel column (5-15% ethyl acetate in hexanes) to give the title compound as a yellow solid. LC/MS m/z=421.2 [M+H]+.

Workup

  1. temperatureunder reflux for 30 min
  2. concentrationConcentrated
  3. customthe residue was purified by chromatography on silica gel column (5-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9da4c74fd547469fa13e05bfad67b068
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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