Pyrrole → 1-(1H-inden-2-yl)-1H-pyrrole

HRID 1178688Notes

Reaction equation

HRID 1178688 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH2:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[NH:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.COCCOC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[C:10]1[N:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1

Participants

8

Reactant 4

HCID 8027PyrroleHCID 62657Potassium Phosphate, TribasicHCID 5755861H-Indene, 2-bromo-HCID 27342152-(Di-tert-butylphosphino)biphenyl

Product 1

HCID 180083501-(1H-inden-2-yl)-1H-pyrroleYield 20.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In three-necked round-bottom flask (1 L), equipped with an Allihn condenser and magnetic stirrer bar and under an argon atmosphere, to a mixture of 49.0 g (231 mmol) of anhydrous K3PO4, 30.0 g (154 mmol) of 2-bromo-1H-indene, and 11.5 ml (11.1 g, 165 mmol) of pyrrole in 500 ml of toluene and 50 ml of DME, 4.59 g (15.4 mmol) of 2-[di(tert-butyl)-phosphino]biphenyl and 1.73 g (7.70 mmol) of Pd(OAc)2 were added at ambient temperature. This mixture was stirred at room temperature for 72 hours. The reaction mixture was filtered through the layer (d 100 mm, l 40 mm) of SilicaGel 60 (40-63 um) on a glass frit funnel. The SilicaGel layer was additionally washed by 200 ml of methyl-tert-butyl ether (MTBE). The combined extract was evaporated to dryness. The crude product was purified using flash chromatography (SilicaGel 60, 40-63 um, d 40 mm, l 500 mm; eluent hexanes/MTBE=10/1). This procedure gave 5.62 g (20%) of white crystalline product.

Workup

  1. additionwere added at ambient temperature
  2. filtrationThe reaction mixture was filtered through the layer (d 100 mm, l 40 mm) of SilicaGel 60 (40-63 um) on a glass frit funnel
  3. washThe SilicaGel layer was additionally washed by 200 ml of methyl-tert-butyl ether (MTBE)
  4. extractionThe combined extract
  5. customwas evaporated to dryness
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-90d04e757c624e5ea51d0202a0dde992
Source dataset
uspto-grants-2007_10
Patent number
US07276567B2

Reaction notes

Loading…