Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17439

反応式

HRID 17439 の反応式
Br[C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([N:9]([CH3:11])[CH3:10])=[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>[CH2:26]([O:25][C:23]([C:2]1[C:3]([F:17])=[C:4]2[O:8][C:7]([N:9]([CH3:11])[CH3:10])=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14])=[CH2:24])[CH3:27]

参加物

6

反応物 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 685849786-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685855916-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile収率 66%

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-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-168) (0.80 g, 2.68 mmol) was dissolved in toluene (25 ml), then tributyl(1-ethoxyvinyl)tin (1.30 ml, 3.85 mmol), 2,6-di-tert-butylcresol (12 mg, 0.05 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.10 g, 0.14 mmol) were added followed by heating under reflux for 3 days. The insoluble matter was removed by filtration through Celite, followed by washing with ethyl acetate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1) to obtain a brown solid (0.51 g, 66%).

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 3 days
  3. customThe insoluble matter was removed by filtration through Celite
  4. washby washing with ethyl acetate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:hexane=1:2 to 2:3 to 9:1 to dichloromethane:methanol=200:1)

出典と根拠

ORDレコード
ord-9295067eed32455cb27d4142ccdc3865
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

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