Lithium Chloride → HCID 67528323, compound

HRID 1867546Notes

Reaction equation

HRID 1867546 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[C:11](=[O:12])[CH2:10][O:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Sn](CCCC)(CCCC)CCCC.[Cl-].[Li+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[C:11](=[O:12])[CH2:10][O:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 67529065HCID 67529065, compound

Product 1

HCID 67528323HCID 67528323, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, a mixture of 0.59 g (2.18 mmol) of 3-(4-bromobenzyl)-1,3-oxazolidine-2,4-dione, obtained in step 9.1., 1.60 g (4.35 mmol) of pyridin-2-yltri-n-butylstannane, 0.28 g (6.6 mmol) of lithium chloride and 0.125 g (0.10 mmol) of palladium tetrakis(triphenylphosphine) in 15 ml of toluene is heated at reflux overnight. It is cooled to ambient temperature, filtered on paper and rinsed in succession with 10 ml of toluene, 10 ml of ethyl acetate and 10 ml of toluene. The filtrates are concentrated under reduced pressure. The residue is taken up in 50 ml of acetonitrile and washed with four times 25 ml of n-hexane. The acetonitrile phase is concentrated under reduced pressure and the residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 mixture of cyclohexane and ethyl acetate.

Workup

  1. customobtained in step 9.1
  2. temperatureat reflux overnight
  3. filtrationfiltered on paper
  4. washrinsed in succession with 10 ml of toluene, 10 ml of ethyl acetate and 10 ml of toluene
  5. concentrationThe filtrates are concentrated under reduced pressure
  6. washwashed with four times 25 ml of n-hexane
  7. concentrationThe acetonitrile phase is concentrated under reduced pressure
  8. customthe residue is purified by chromatography on silica gel
  9. washeluting with a 70/30
  10. addition60/40 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-cff025a1014344cea7dd89c9242f1e9a
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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