Indole → HCID 178467346, compound

HRID 1489779Notes

Reaction equation

HRID 1489779 reaction equation
C(O[CH2:5][C:6]1[NH:7][C:8]([C:15](=[O:17])[CH3:16])=[C:9]([CH3:14])[C:10]=1[C:11](=O)[CH3:12])(=O)C.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>ClC(Cl)C>[C:15]([C:8]1[C:9]([CH3:14])=[C:10]2[C:6]([N:7]=1)=[CH:5][C:20]1[C:19]([N:18]=[C:26]3[C:21]=1[CH:22]=[CH:23][CH:24]=[CH:25]3)=[C:11]2[CH3:12])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 798IndoleHCID 22902273HCID 22902273, compoundHCID 71586775Bentonite

Product 1

HCID 178467346HCID 178467346, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-acetoxymethyl-3,5-diacetyl-4-methylpyrrole (0.200 g) and indole (0.098 g) in dichloroethane (90 cm3) was added Montmorillonite K10 clay (0.30 g). The mixture was stirred and heated at reflux for 80 h. After cooling the clay was removed by filtration and the filtrate concentrated to ca 20 cm3 in vacuo. The crude product was removed by filtration and then chromatographed on silica. Elution with chloroform-methanol (60:1) yielded 0.08 g of the title compound as a yellow solid m.p. 258°-260° C., m/z (EI) 276 (M+) δH ([2H6 ]-DMSO) 2.58 (3H, s, COCH3), 2.88 (3H, s, CH3), 2.92 (3H, s, CH3), 7.05 (1H, m, 8-H), 7.38 (2H, m, 6-H, 7-H), 7.85 (1H, s, 10-H), 8.08(1H, J, 8 Hz, 9-H), 10.6 (1H, s, NH), 11.17 (1H, s, NH). (Found: C, 77.0; H, 5.74; N, 9.76; C18H16N2 O. 0.14 EtOAc requires C, 77.2; H, 5.98; N, 9.70%.)

Workup

  1. temperatureheated
  2. temperatureat reflux for 80 h
  3. temperatureAfter cooling the clay
  4. customwas removed by filtration
  5. concentrationthe filtrate concentrated to ca 20 cm3 in vacuo
  6. customThe crude product was removed by filtration
  7. customchromatographed on silica
  8. washElution with chloroform-methanol (60:1)

Sources & evidence

ORD record
ord-6b52fc556dee42dcad8bb297d851bb6a
Source dataset
uspto-grants-1997_10
Patent number
US05679694

Reaction notes

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