2-(4-Bromo-3-methylphenyl)-5-methyl-1,3,4-oxadiazole → HCID 22115880, compound

HRID 1276292Notes

Reaction equation

HRID 1276292 reaction equation
C[Sn](C)(C)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)=[CH:18][C:17]=1[CH3:28]>C1(C)C=CC=CC=1.[Pd](Cl)Cl.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>[CH3:28][C:17]1[CH:18]=[C:19]([C:22]2[O:23][C:24]([CH3:27])=[N:25][N:26]=2)[CH:20]=[CH:21][C:16]=1[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 114366932-(4-Bromo-3-methylphenyl)-5-methyl-1,3,4-oxadiazoleHCID 22742033HCID 22742033, compound2×

Product 1

HCID 22115880HCID 22115880, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

Methyl 6-(trimethylstannyl)nicotinate (D11, 0.300 g, 1.00 mmol) was dissolved in dry toluene (15 ml) and was treated with 2-(4-bromo-3-methylphenyl)-5-methyl-1,3,4-oxadiazole (EP 0533268A1) (0.211 g, 0.834 mmol). The mixture was flushed with argon and bis(triphenyl phosphine)pallalladium (II) chloride (0.029 g, 0.042 mmol) was added. The mixture was then heated to reflux under argon. After 2 h, further methyl 6-(trimethylstannyl)nicotinate (0.030 g, 0.100 mmol) in toluene (2 ml) and bis(triphenylphosphine) palladium (II) chloride (0.010 g, 0.014 mmol) was added. Reflux was continued for a further 2 h before the reaction mixture was allowed to cool. The reaction mixture was then filtered through kieselguhr. The kieselguhr was washed with toluene (2×20 ml) and the filtrate was evaporated under reduced pressure to give a yellow/brown solid which was dried in vacuo (0.450 g). The solid was then purified by silica-gel chromatography (1:1 Petrol 60-80: EtOAc as eluant) to give the title compound as a cream coloured solid (0.140 g, 54%).

Workup

  1. additionwas added
  2. temperatureThe mixture was then heated
  3. temperatureto reflux under argon
  4. temperatureReflux
  5. waitwas continued for a further 2 h before the reaction mixture
  6. temperatureto cool
  7. filtrationThe reaction mixture was then filtered through kieselguhr
  8. washThe kieselguhr was washed with toluene (2×20 ml)
  9. customthe filtrate was evaporated under reduced pressure
  10. customto give a yellow/brown solid which
  11. customwas dried in vacuo (0.450 g)
  12. customThe solid was then purified by silica-gel chromatography (1:1 Petrol 60-80: EtOAc as eluant)

Sources & evidence

ORD record
ord-542ad1a9e96340a5b0c20e4b1d288b71
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Reaction notes

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