Cesium carbonate → HCID 66980978, compound

HRID 2279255Notes

Reaction equation

HRID 2279255 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH3:14][N:15]1[CH2:19][C@H:18]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[NH:17][C:16]1=[O:30].C([O-])([O-])=O.[Cs+].[Cs+].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>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]>[CH2:23]([O:22][C:20]([C@H:18]1[CH2:19][N:15]([CH3:14])[C:16](=[O:30])[N:17]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1)=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 223378254-Bromo-2-(trifluoromethyl)benzonitrileHCID 50999035HCID 50999035, compound

Product 1

HCID 66980978HCID 66980978, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromo-2-(trifluoromethyl)benzonitrile (0.1 g, 0.4 mmol) dissolved in 1,4-Dioxane (5 mL), (R)-benzyl 1-methyl-2-oxoimidazolidine-4-carboxylate (25c) (0.093 g, 0.4 mmol) was added at room temperature followed by Cs2CO3 (0.260 g, 0.8 mmol) and Argon gas was purged for 30 min. To the reaction mixture Pd2(dba)3 (0.036 g, 0.04 mmol) and Xanthphos (0.034 g, 0.058 mmol) were added at room temperature. The resulting reaction mixture was then heated to 100° C. for 5 h. After completion (by TLC), the reaction mixture was filtered through celite bed. The celite bed was washed with EtOAc (2×5 mL), the filtrates were combined, dried over Na2SO4 and concentrated under reduced pressure to give the crude compound. The crude residue was purified by column chromatography to provide 25d (0.075 g, 46%) as a colourless syrup.

Workup

  1. customwas purged for 30 min
  2. customThe resulting reaction mixture
  3. filtrationAfter completion (by TLC), the reaction mixture was filtered through celite bed
  4. washThe celite bed was washed with EtOAc (2×5 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude compound
  8. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-0a94b168c402498bab4b927b1b9cf26b
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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