Triphenylarsine → HCID 11069390, compound

HRID 2289581Notes

Reaction equation

HRID 2289581 reaction equation
CN1CCCC1=O.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Sn](C)(C)[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH2:39][CH:38]([CH2:40][NH:41][C:42](=[O:44])[CH3:43])[O:37][N:36]=2)=[CH:31][CH:30]=1.[CH3:47][C:48]([O:51][C:52]([N:54]1[CH2:59][CH:58]=[C:57](OS(C(F)(F)F)(=O)=O)[CH2:56][CH2:55]1)=[O:53])([CH3:50])[CH3:49]>C(OCC)(=O)C.O.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]>[C:42]([NH:41][CH2:40][CH:38]1[O:37][N:36]=[C:35]([C:32]2[CH:33]=[CH:34][C:29]([C:57]3[CH2:58][CH2:59][N:54]([C:52]([O:51][C:48]([CH3:50])([CH3:49])[CH3:47])=[O:53])[CH2:55][CH:56]=3)=[CH:30][CH:31]=2)[CH2:39]1)(=[O:44])[CH3:43]

Participants

8

Reactant 4

HCID 11773TriphenylarsineHCID 13387N-methyl-2-pyrrolidoneHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 11090216HCID 11090216, compound

Product 1

HCID 11069390HCID 11069390, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flame dried flask containing a pre-stirred slurry of 1-methyl-2-pyrrolidinone (15 mL), tris(dibenzylideneacetone)dipalladium (30 mg, 0.03 mmol), triphenylarsine (4 mg, 0.12 mmol) under an inert atmosphere is added N-[[4,5-dihydro-3-[4-(trimethylstannyl)phenyl]-5-isoxazolyl]methyl]acetamide (580 mg, 1.52 mmol) and 3,6-dihydro-4-[[(trifluoromethyl)sulfonyl]oxy]-1(2H)-pyridinecarboxylic acid 1,1-dimethylethyl ester (450 mg, 1.37 mmol) and stirred for 12 hours. The reaction is diluted with ethyl acetate (100 mL) and water (50 mL). The organic phase is separated, extracted with water (5×50 mL), dried over sodium sulfate, concentrated in vacuo and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with methylene chloride/methanol (99/1). The appropriate fractions are combined (Rf =0.28, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, mp 117-120° C.

Workup

  1. customTo a flame dried flask
  2. customThe organic phase is separated
  3. extractionextracted with water (5×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (230-400 mesh, 100 mL)
  7. washeluting with methylene chloride/methanol (99/1)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54566ca61b1b4c3a85c9860d138309d2
Source dataset
uspto-grants-2000_07
Patent number
US06093736

Reaction notes

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