Cesium carbonate → HCID 58234931, compound

HRID 1365865Notes

Reaction equation

HRID 1365865 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1OS(C(F)(F)F)(=O)=O)=[O:5])C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:26]([NH:33][C:34]([NH2:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCOCC1.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].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH2:26]([N:33]1[C:4](=[O:5])[C:6]2[S:10][C:9]([CH3:11])=[N:8][C:7]=2[NH:36][C:34]1=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 10853BenzylureaHCID 21064930HCID 21064930, compound

Product 1

HCID 58234931HCID 58234931, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-methyl-4-(trifluoromethanesulfonyloxy)thiazole-5-carboxylic acid ethyl ester (6.38 g, 20 mmol) in dioxane (80 mL) under an atmosphere of N2 was added cesium carbonate (13.0 g, 40 mmol), benzylurea (3.3 g, 22 mmol), Xantphos (0.58 g, 0.1 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.46 g, 0.5 mmol). The resulting mixture was stirred at 60° C. for 18 h, cooled to RT, then poured onto water (500 mL) and stirred for 15 min. The resulting mixture was filtered, the filtrate collected and reduced in volume in vacuo to approximately one-third. The resultant precipitate was collected by filtration, washed with ether and dried in vacuo to give the title compound as a white solid (3.9 g, 72%).

Workup

  1. temperaturecooled to RT
  2. additionpoured onto water (500 mL)
  3. stirringstirred for 15 min
  4. filtrationThe resulting mixture was filtered
  5. customthe filtrate collected
  6. filtrationThe resultant precipitate was collected by filtration
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-cc46ae44fc704a53b714f722cf660682
Source dataset
uspto-grants-2011_02
Patent number
US07893060B2

Reaction notes

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