Cesium carbonate → HCID 67009927, compound

HRID 2194529Notes

Reaction equation

HRID 2194529 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.[NH2:19][C:20]1[CH:24]=[C:23]([CH3:25])[O:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=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]>[CH3:25][C:23]1[O:22][N:21]=[C:20]([NH:19][C:7]2[N:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[CH:24]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 661723-Amino-5-methylisoxazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11716156HCID 11716156, compound

Product 1

HCID 67009927HCID 67009927, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

6.7 g (24 mmol) of methyl 2-(trifluoromethylsulfonyloxy)nicotinate and 3.0 g (31 mmol) of 3-amino-5-methylisoxazole were dissolved in toluene (100 mL), and 13.1 g (40 mmol) of cesium carbonate, 1.5 g (1.6 mmol) of tris(dibenzylideneacetone)dipalladium(0), and 1.9 g (3.4 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were added to the solution. The resulting mixture was heated and stirred for one hour at 80° C. The reaction mixture was cooled, and then the solvent was distilled off. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4), and thus 4.3 g of the title compound was obtained as an orange-colored viscous product (yield: 78%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-5b2ce16828e842089bbc41adafabdaaf
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

Loading…