Stannane, tributyl(1-ethoxyethenyl)- → 2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17336

반응식

HRID 17336 반응식
Br[C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].C([Sn](CCCC)(CCCC)[C:23]([O:25][CH2:26][CH3:27])=[CH2:24])CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(C1(C)C(O)=C(C(C)(C)C)C=CC1)(C)(C)C>[CH:9]1([C:7]2[O:8][C:4]3[C:5](=[C:12]([C:15]#[N:16])[C:13]([CH3:14])=[C:2]([C:23]([O:25][CH2:26][CH3:27])=[CH2:24])[C:3]=3[F:17])[N:6]=2)[CH2:11][CH2:10]1

참가 물질

6

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

생성물 1

HCID 685864422-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile수율 108.5%

시약·촉매·용매 3

HCID 666371922,6-Di-t-butylcresol촉매HCID 178418476HCID 178418476, 화합물촉매HCID 1140Toluene용매

실험 절차

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (8.88 g, 30.08 mmol) was dissolved in toluene (130 ml), then tributyl(1-ethoxyvinyl)tin (11.2 ml, 33.09 mmol) and 2,6-di-tert-butylcresol (66 mg, 0.30 mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.06 g, 1.50 mmol) were added, followed by heating under reflux for 17 hours under nitrogen atmosphere. The reaction liquid was cooled, the insoluble matter was separated by filtration through Celite, the solvent was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, followed by removing tin-derived side products with n-hexane and by elution with a mixed solvent of n-hexane/ethyl acetate (7:1, v/v) to obtain the a crude product (9.34 g, quant.) as a yellow white solid.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 17 hours under nitrogen atmosphere
  3. customThe reaction liquid
  4. temperaturewas cooled
  5. customthe insoluble matter was separated by filtration through Celite
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customby removing tin-
  8. washby elution with a mixed solvent of n-hexane/ethyl acetate (7:1

출처 및 근거

ORD 기록
ord-bc7ab6ec423e4978a7320d1f5439a7aa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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