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

HRID 17336

反応式

HRID 17336 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 666371922,6-Di-t-butylcresol触媒HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bc7ab6ec423e4978a7320d1f5439a7aa
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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