2-(Tributylstannyl)furan → 7-(2-Furyl)-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole

HRID 1007365Notes

Reaction equation

HRID 1007365 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]1[O:27][CH:28]=[CH:29][CH:30]=1)CCC>CC1C=CC(C)=CC=1.[Cl-].[NH4+].CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[O:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 121489697-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole

Product 1

HCID 219073927-(2-Furyl)-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazoleYield 99%

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 7809P-XyleneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

7-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (300 mg, 0.90 mmol) and dichlorobis(tri-o-tolylphosphine)palladium(II) (71 mg, 0.09 mmol) were dissolved in p-xylene (3 mL) and stirred for 10 min at room temperature under a nitrogen atmosphere. 2-(Tributylstannyl)furan (449 mg, 1.26 mmol) was added and the mixture was refluxed for 4 hours. The mixture was cooled to room temperature, diluted with a saturated solution of ammonium chloride and extracted with EtOAc. The organic extracts were washed with water, then brine and dried over MgSO4 and concentrated. Purification by flash chromatography (20%-30% EtOAc/petroleum ether) gave the title compound as a white solid (99% yield, m.p 120-121° C.); MS m/e 322 (M+H)+.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with EtOAc
  4. washThe organic extracts were washed with water
  5. dry with materialbrine and dried over MgSO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20%-30% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-e9901114742246aeaec9e47ae8f6dd76
Source dataset
uspto-grants-2004_09
Patent number
US06794403B2

Reaction notes

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