Triphenylarsine → 3-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one

HRID 1826457Notes

Reaction equation

HRID 1826457 reaction equation
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC.[CH2:39]([N:45]1[CH2:50][CH:49]2[CH:47]([C:48]2([C:52]2[CH:57]=[CH:56][CH:55]=[C:54](I)[CH:53]=2)[CH3:51])[C:46]1=[O:59])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>O1CCCC1.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]>[CH2:39]([N:45]1[CH2:50][CH:49]2[CH:47]([C:48]2([CH3:51])[C:52]2[CH:57]=[CH:56][CH:55]=[C:54]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:53]=2)[C:46]1=[O:59])[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 6077842-(Tributylstannyl)pyridineHCID 221412913-Hexyl-6-(3-iodophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221412333-Hexyl-6-methyl-6-[3-(2-pyridinyl)phenyl]-3-azabicyclo[3.1.0]hexan-2-oneYield 101.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To tris(dibenzylideneacetone)dipalladium (0) (4.4 mg, 4.80 μmol) in tetrahydrofuran (1 ml) at room temperature was added triphenylarsine (5.9 mg, 19.2 μmol). After 5 min, 2-(tributylstannyl)pyridine (0.10 g, 0.29 mmol) in tetrahydrofuran (1 ml) was added followed by 3-hexyl-6-(3-iodophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 67, 77 mg, 0.19 mmol) in tetrahydrofuran (1 ml). The reaction mixture was stirred at room temperature for 16 h and then refluxed for 2 h. The cooled reaction mixture was concentrated in vacuo and chromatographed on silica gel eluting with hexane:ethyl acetate (1:1 then 0:1) to give the title compound as a colourless oil (67 mg, 100%).

Workup

  1. temperaturerefluxed for 2 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customchromatographed on silica gel eluting with hexane:ethyl acetate (1:1

Sources & evidence

ORD record
ord-5cb8d6049f7042caabc1657ca7c708d2
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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