Triphenylarsine → 3-Hexyl-6-methyl-6-[3-(1-triphenylmethyl-1H-imidazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one

HRID 428949Notes

Reaction equation

HRID 428949 reaction equation
C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:26]1[CH2:31][CH:30]2[CH:28]([C:29]2([C:33]2[CH:38]=[CH:37][CH:36]=[C:35](I)[CH:34]=2)[CH3:32])[C:27]1=[O:40])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C([Sn](CCCC)(CCCC)[C:46]1[N:47]=[CH:48][N:49]([C:51]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:50]=1)CCC>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]>[CH2:20]([N:26]1[CH2:31][CH:30]2[CH:28]([C:29]2([CH3:32])[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:50]3[N:49]([C:51]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:64]4[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=4)[C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=4)[CH:48]=[N:47][CH:46]=3)[CH:34]=2)[C:27]1=[O:40])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 118281174-(Tributylstannyl)-1-tritylimidazoleHCID 221412913-Hexyl-6-(3-iodophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221411573-Hexyl-6-methyl-6-[3-(1-triphenylmethyl-1H-imidazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-oneYield 25%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To tris(dibenzylideneacetone)dipalladiunm (0) (8.7 mg, 9.5 mmol) in tetrahydrofuran (2.5 ml) at room temperature was added triphenylarsine (12 mg, 39.2 [mol). After 10 min, a solution of 3-hexyl-6-(3-iodophenyl)-6-methyl-3-azabicyclo[3.1.0]hexan-2-one (Preparation 67, 0.15 g, 3.8 mmol) in tetrahydrofuran (2.5 ml) was added. A minute later, 4-(tributylstannyl)-1-triphenylmethyl-1H-imidazole (Preparation 73, 0.332 g, 0.55 mmol) in tetrahydrofuran (3 ml) was added. The reaction mixture was stirred at room temperature for 30 min and then refluxed for 3.5 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 (55 mg, 25%).

Workup

  1. temperaturerefluxed for 3.5 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-0710cc807b2241e58a88faf5ffdcc07a
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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