5,6,7-Trimethoxy-1H-indole-2-carboxylic acid → HCID 19050056, compound

HRID 1780222Notes

Reaction equation

HRID 1780222 reaction equation
C([O:5][C:6]([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[C:17]([OH:20])[CH:18]=2)[NH:15][C:14]([C:21]([F:24])([F:23])[F:22])=[C:13]3[C:25]([O:27][CH3:28])=[O:26])[CH:10]([CH2:29][Cl:30])[CH2:9]1)=O)(C)(C)C.C(OCC)(=O)C.Cl.[CH3:38][O:39][C:40]1[CH:41]=[C:42]2[C:46](=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[NH:45][C:44](C(O)=O)=[CH:43]2.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[Cl:30][CH2:29][CH:10]1[C:11]2=[C:12]3[C:16](=[C:17]([OH:20])[CH:18]=[C:19]2[N:8]([C:6]([C:44]2[NH:45][C:46]4[C:42]([CH:43]=2)=[CH:41][C:40]([O:39][CH3:38])=[C:48]([O:49][CH3:50])[C:47]=4[O:51][CH3:52])=[O:5])[CH2:9]1)[NH:15][C:14]([C:21]([F:24])([F:22])[F:23])=[C:13]3[C:25]([O:27][CH3:28])=[O:26]

Participants

7

Reactant 4

HCID 8210525,6,7-Trimethoxy-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19050034HCID 19050034, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 19050056HCID 19050056, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 42.6 mg(95 μmol) of methyl 3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate, 1.6 ml of 3M hydrogen chloride-ethyl acetate was added, and the mixture was stirred at room temperature for one hour. Then the solvent was distilled off. The residue with 23.8 mg (95 mol) of 5,6,7-trimethoxyindole-2-carboxylic acid, and 54.6 mg (285 μmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was stirred in 0.95 ml of anhydrous dimethylformamide at room temperature under atmosphere of argon overnight. Water was added to the liquid reaction mixture. The resulting mixture was extracted with methylene chloride, and the extract solution was washed with water, 10% sodium hydrogencarbonate, and saturated sodium chloride solution successively, and dried over anhydrous sodium sulfate. Therefrom the solvent was distilled off. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain methyl 1-chloromethyl-5-hydroxy-7-trifluoromethyl-3-(5,6,7-trimethoxy-1H-indol-2-ylcarbonyl)-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 45.3 mg (82%).

Workup

  1. distillationThen the solvent was distilled off
  2. extractionThe resulting mixture was extracted with methylene chloride
  3. washthe extract solution was washed with water, 10% sodium hydrogencarbonate, and saturated sodium chloride solution successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationTherefrom the solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-2210770b1822481c8d4cebc3bc8c4f7e
Source dataset
uspto-grants-1997_05
Patent number
US05629430

Reaction notes

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