Triphenylarsine → HCID 57429282, compound

HRID 1435894Notes

Reaction equation

HRID 1435894 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[C:9]3[N:13]([C:6]=2[CH:5]=[CH:4][N:3]=1)[CH2:12][CH2:11][C:10]3=[O:14].[C:15]1([As](C2C=CC=CC=2)C2C=CC=CC=2)[CH:20]=CC=C[CH:16]=1.C([Sn](CCCC)(CCCC)C(C)=C)CCC>CN(C=O)C.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:15]([C:2]1[C:7]2[CH:8]=[C:9]3[N:13]([C:6]=2[CH:5]=[CH:4][N:3]=1)[CH2:12][CH2:11][C:10]3=[O:14])([CH3:20])=[CH2:16]

Participants

6

Reactant 3

HCID 11773TriphenylarsineHCID 10871254Stannane, tributyl(1-methylethenyl)-HCID 57429281HCID 57429281, compound

Product 1

HCID 57429282HCID 57429282, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
78 °C

Procedure

To a mixture of 1-chloro-6,7-dihydro-8H-pyrido[3,4-b]pyrrolizin-8-one (5.0 g, 24.3 mmol), tris (dibenzylidene acetone)dipalladium (0) (1.0 g, 1.09 mmol) and triphenylarsine (2.70 g, 8.82 mmol) in DMF (100 mL) was added tributylisopropenyl stannane (9.60 g, 29.00 mmol). The resulting mixture was degassed and heated at 78° C. for a period of 18 h. The solvant was evaporated under reduced pressure. CH2Cl2 and celite were added to the resulting mixture which was then filtered over celite. The title compound was purified by flash chromatography (50% to 100% EtOAc in Hexane).

Workup

  1. customThe resulting mixture was degassed
  2. customThe solvant was evaporated under reduced pressure
  3. additionCH2Cl2 and celite were added to the resulting mixture which
  4. filtrationwas then filtered over celite
  5. customThe title compound was purified by flash chromatography (50% to 100% EtOAc in Hexane)

Sources & evidence

ORD record
ord-b5c5bb9d4e824304af14014ec2545e4a
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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