Potassium Fluoride → HCID 59820948, compound

HRID 1363663Notes

Reaction equation

HRID 1363663 reaction equation
Cl[C:2]1[C:3]([O:28][CH3:29])=[CH:4][C:5]([O:26][CH3:27])=[C:6]([N:8]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[F:30][C:31]([F:43])([F:42])[O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCCC1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:8]([C:6]2[C:5]([O:26][CH3:27])=[CH:4][C:3]([O:28][CH3:29])=[C:2]([C:36]3[CH:35]=[CH:34][C:33]([O:32][C:31]([F:30])([F:42])[F:43])=[CH:38][CH:37]=3)[CH:7]=2)[C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:21][CH:20]=1)([CH3:23])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 58008110HCID 58008110, compound

Product 1

HCID 59820948HCID 59820948, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl N-(5-chloro-2,4-dimethoxyphenyl)-N-[4-(tert-butyl)benzyl]oxamate (800 mg, 1.91 mmol), 4-(trifluoromethoxy)benzeneboronic acid (549 mg, 2.67 mmol), palladium(II) acetate (21 mg, 0.095 mmol), potassium fluoride (332 mg, 5.72 mmol), 2-(di-tert-butylphosphino)biphenyl (57 mg, 0.191 mmol) and tetrahydrofuran (3.0 ml) was refluxed for 5 hours under argon atmosphere. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (140 mg, 14%) as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 5 hours under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-9447cb523ef8469bac3fad09c7679bd7
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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