Methanol → HCID 5327660, compound

HRID 345674Notes

Reaction equation

HRID 345674 reaction equation
[N:1]1([C:10]2[C:11](=[O:26])O[C:13](=[O:25])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH3:24])[CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Si](C)(C)[NH:29][Si](C)(C)C.CO>C1(C)C=CC=CC=1>[N:1]1([C:10]2[C:11](=[O:26])[NH:29][C:13](=[O:25])[C:14]=2[C:15]2[C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:17]([CH3:24])[CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 13838HexamethyldisilazaneHCID 14784930HCID 14784930, compound

Product 1

HCID 5327660HCID 5327660, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture, 163 mg of 3-(1-indolyl)-4-(1-methyl-3-indolyl)furan-2,5-dione, 2.6 g of hexamethyldisilazane, 0.6 g of methanol and 50 ml of toluene was stirred at 40° C. for 1 hour and then at 110° C. for 1 hour. The mixture was evaporated and the residue was chromatographed on silica gel with 10% methanol in dichloromethane to give 75 mg of 3-(1-indolyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 235°-236° C.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was chromatographed on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-b833859d1aae44d5b328111193f8004a
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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