Tri-o-tolylphosphine → HCID 20751575, compound

HRID 722774Notes

Reaction equation

HRID 722774 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:5]2.C[O-].[CH2:24]([Sn+](CCCC)CCCC)[CH2:25][CH2:26]C.C(CC([O-])=[O:44])=CC(=C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1(C)C=CC=CC=1.C(OCC)(=O)C.[F-].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:44]=[C:25]([CH3:26])[CH2:24][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:5]2

Participants

9

Reactant 4

HCID 80271Tri-o-tolylphosphineHCID 11964040Methoxytri-n-butylstannaneHCID 20751576HCID 20751576, compoundHCID 73472294HCID 73472294, compound

Product 1

HCID 20751575HCID 20751575, compoundYield 77.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 522689Potassium FluorideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-tert-butyl 2-methyl 5-bromo-1H-indole-1,2-dicarboxylate (Preparation 18, 12.5 g, max 32.04 mmol), tributyltin methoxide (11.0 ml, 38.2 mmol), isoprenylacetate (5.3 ml, 48.1 mmol), palladium acetate (0.36 g, 5 mol %), tri-o-tolylphosphine (0.97 g, 10 mol %) in toluene (40 ml) was degassed and then heated at 100° C. for 8 hours. The reaction mixture was diluted with ethyl acetate (50 ml), 4M potassium fluoride (aqueous, 100 ml) and left to stir at room temperature overnight. The resulting mixture was filtered through arbocel washing the precipitate thoroughly with ethyl acetate (100 ml) and the organic phase of the filtrate separated, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (95:5 changing to 90:10, by volume) to give the title compound (8.2 g) as a yellow oil.

Workup

  1. waitleft
  2. filtrationThe resulting mixture was filtered through arbocel washing the precipitate thoroughly with ethyl acetate (100 ml)
  3. customthe organic phase of the filtrate separated
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (95:5 changing to 90:10, by volume)

Sources & evidence

ORD record
ord-3b658dd4d7ac48bd928e22d62090e8e5
Source dataset
uspto-grants-2006_11
Patent number
US07138527B2

Reaction notes

Loading…