Cesium carbonate → HCID 67009517, compound

HRID 2194540Notes

Reaction equation

HRID 2194540 reaction equation
FC(F)(F)S(O[C:7]1[N:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])(=O)=O.C1COC2C=CC(C[NH2:25])=CC=2O1.[C:31](=[O:34])([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)[C:44]2[C:57]3[O:56][C:55]4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)[C:48]=3[CH:47]=[CH:46][CH:45]=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:34]1[CH2:31][CH2:55][O:56][C:57]2[CH:44]=[C:45]([NH:25][C:7]3[N:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9]([O:11][CH3:12])=[O:10])[CH:46]=[CH:47][C:48]1=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 871022,3-Dihydro-1,4-benzodioxin-6-methylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11716156HCID 11716156, compound

Product 1

HCID 67009517HCID 67009517, compoundYield 662.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

10.6 g (37 mmol) of methyl 2-(trifluoromethylsulfonyloxy)nicotinate and 6.2 g (41 mmol) of 3,4-ethylenedioxybenzylamine were dissolved in toluene (100 mL), and 17.0 g (52 mmol) of cesium carbonate, 1.0 g (1.1 mmol) of tris(dibenzylideneacetone)dipalladium(0), and 1.3 g (5.2 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added thereto. The resulting mixture was heated and stirred for 2 hours at 80° C. The solvent was distilled off from the reaction mixture, water and ethyl acetate were added to the residue, and the resulting mixture was filtered. The filtrate was extracted with ethyl acetate, and the organic phase was washed with an aqueous solution of citric acid and water in this order, and then was dried and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:9 to 1:2), and thus 9.86 g of the title compound was obtained as an orange-colored viscous product (yield: 93%).

Workup

  1. temperatureThe resulting mixture was heated
  2. distillationThe solvent was distilled off from the reaction mixture, water and ethyl acetate
  3. additionwere added to the residue
  4. filtrationthe resulting mixture was filtered
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe organic phase was washed with an aqueous solution of citric acid and water in this order
  7. customwas dried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:9 to 1:2)

Sources & evidence

ORD record
ord-5ba362b6e4a74856a33c32a66ad166e1
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

Loading…