Methanol → 2-(1,3-Benzodioxol-5-yl)-2-(6-methoxycarbonyl-1-methyl-1H-indol-3-yl)acetic acid

HRID 322089

Reaction equation

HRID 322089 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=2)[CH:11]=[CH:10]1.CO.[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([CH:33](O)[C:34]([OH:36])=[O:35])=[CH:32][C:27]=2[O:26][CH2:25]1>C(#N)C>[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([CH:33]([C:11]3[C:12]4[C:17](=[CH:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:13]=4)[N:9]([CH3:8])[CH:10]=3)[C:34]([OH:36])=[O:35])=[CH:32][C:27]=2[O:26][CH2:25]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 1196183',4'-Methylenedioxymandelic acidHCID 639843Methyl N-methylindole-6-carboxylate

Product 1

HCID 220099412-(1,3-Benzodioxol-5-yl)-2-(6-methoxycarbonyl-1-methyl-1H-indol-3-yl)acetic acidYield 80.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoroacetic acid (1.92 kg) was added portionwise to a stirred suspension of methyl 1-methyl-1H-indole-6-carboxylate (prepared by the same method as 1-methylindole-6-tert-butyl ester in Example 28, International Patent Application WO 97/43260, but using methanol in place of 6-tert-butanol; 1.63 kg) and 2-(1,3-benzodioxol-5-yl)-2-hydroxyacetic acid (1.67 kg) in acetonitrile (16.3 liters) at room temperature under a nitrogen atmosphere. The suspension was heated to reflux for 24 h and allowed to cool to room temperature. Filtration of the precipitated product gave the subtitle compound as a white crystalline solid (2.54 kg, 80.4%).

Workup

  1. customat room temperature
  2. temperatureThe suspension was heated
  3. temperatureto reflux for 24 h
  4. filtrationFiltration of the precipitated product

Sources & evidence

ORD record
ord-b4294ca46df344a9b0f6377b2516edd0
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Linked notes

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