Potassium Carbonate → Methyl N-(3,5-dimethylbenzyl)-N-[4'-(trifluoromethoxy)biphenyl-4-yl]oxamate

HRID 1363648Notes

Reaction equation

HRID 1363648 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)[C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe].O>[CH3:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([CH3:22])[CH:19]=1)[CH2:15][N:8]([C:5]1[CH:6]=[CH:7][C:2]([C:30]2[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:36])[F:37])=[CH:32][CH:31]=2)=[CH:3][CH:4]=1)[C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 59820918methyl N-(4-bromophenyl)-N-(3,5-dimethylbenzyl)oxamate

Product 1

HCID 59820911Methyl N-(3,5-dimethylbenzyl)-N-[4'-(trifluoromethoxy)biphenyl-4-yl]oxamateYield 73.3%

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl N-(4-bromophenyl)-N-(3,5-dimethylbenzyl)oxamate (707 mg, 1.88 mmol), 4-(trifluoromethoxy)phenylboronic acid (500 mg, 2.44 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (300 mg, 0.357 mmol), potassium carbonate (389 mg, 2.82 mmol), dioxane (10 ml) and water (1 ml) was stirred at 80° for 4 hours. The reaction mixture was cooled to room temperature, and filtered through celite. The residue obtained by concentration of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1) to give the title compound (630 mg, 73%) as a light brown oil.

Workup

  1. filtrationfiltered through celite
  2. customThe residue obtained by concentration of the filtrate under reduced pressure
  3. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ff4e045a8ed04ff0a513b5dfaf14189c
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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