تفاعل #1596953

ord-70088dc7e64e46b5b9ca0cd3fc0d6742

معادلة التفاعل

Brc1cccc2oc3ccccc3c12
bromodibenzofuran
Brc1cccc2oc3ccccc3c12
Compound 16-1
Brc1cccc2oc3ccccc3c12
bromodibenzofuran
c1cn[nH]c1
pyrazole
ON=Cc1ccccc1O
salicylaldoxime
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
c1ccc2c(c1)oc1cccc(-c3cc[nH]n3)c12
Compound 17-1
المردود 78.0%
c1ccc2c(c1)oc1cccc(-c3cc[nH]n3)c12
Pyrazolyldibenzofuran
المردود 78.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىis reacted
  2. 2
    درجة الحرارةunder reflux
  3. 3
    درجة الحرارةwith heating for 6 hours
  4. 4
    workup.DISTILLATIONDMF is distilled off from the resulting mixture
  5. 5
    درجة الحرارةby heating under reduced pressure
  6. 6
    workup.ADDITIONEthyl acetate is added to the residue
  7. 7
    ترشيحthe mixture is filtered with Celite
  8. 8
    workup.ADDITIONa 1M sodium hydroxide aqueous solution is added to the obtained liquid
  9. 9
    استخلاصOrganic layers extracted from the obtained mixture with ethyl acetate
  10. 10
    تجفيفare dried with sodium sulfate
  11. 11
    تركيزThe organic layers are concentrated

الإجراء التجريبي

Under nitrogen current, a mixture containing 12.35 g (50 mmol) of bromodibenzofuran (Compound 16-1), 5.11 g (75 mmol) of pyrazole, 358 mg (2.5 mmol) of cuprous oxide (I), 1.37 g (10 mmol) of salicylaldoxime, 32.6 g (100 mmol) of cesium carbonate, and 100 ml of DMF is reacted under reflux with heating for 6 hours. DMF is distilled off from the resulting mixture by heating under reduced pressure. Ethyl acetate is added to the residue and the mixture is filtered with Celite, and a 1M sodium hydroxide aqueous solution is added to the obtained liquid. Organic layers extracted from the obtained mixture with ethyl acetate are dried with sodium sulfate. The organic layers are concentrated and refined by silica gel column chromatography to obtain 9.12 g (39 mmol) of Compound 17-1.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08211551B2uspto-grants-2012_07