Triphenylphosphine → HCID 123876700, compound

HRID 712674Notes

Reaction equation

HRID 712674 reaction equation
[CH3:1][S:2]([CH2:5][CH:6]=[CH2:7])(=[O:4])=[O:3].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13](Br)[CH:14]=1.CC([O-])=O.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:7]=[CH:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:14]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 1400483-(Methylsulphonyl)-1-propeneHCID 517045Sodium Acetate

Product 1

HCID 123876700HCID 123876700, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Methanesulfonyl-propene (2.4 g, 20 mmol), 3,5-dibromo-pyridine (4.7 g, 20 mmol), NaOAc (1.9 g, 60 mmol), PPh3 (1.6 g, 6.0 mmol) and Pd(OAc)2 (450 mg, 2.0 mmol) are mixed in 1,4-dioxane (350 ml) and heated to reflux for 16 hrs. The reaction mixture is filtered and the filtrate is concentrated. The residue is taken up in DCM and washed with water. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by flash column chromatography to give 2.0 g of 3-bromo-5-(-3-methanesulfonyl-propenyl)-pyridine with some PPh3O.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hrs
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. washwashed with water
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-833c474a4a0a4adb9b3f78dfc73dae3c
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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