Ammonium fluoride → 3-Amino-4-(thiophen-2-yl)-6-bromophthalimide

HRID 21001

反応式

HRID 21001 の反応式
[NH2:1][C:2]1[C:12](I)=[CH:11][C:10]([Br:14])=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6].C([Sn](CCCC)(CCCC)[C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)CCC.[F-].[NH4+]>C1COCC1.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>[NH2:1][C:2]1[C:12]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][C:10]([Br:14])=[C:4]2[C:5]([NH:7][C:8](=[O:9])[C:3]=12)=[O:6]

参加物

6

反応物 3

HCID 25516Ammonium fluorideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 684887173-Amino-4-iodo-6-bromophthalimide

生成物 1

HCID 684893823-Amino-4-(thiophen-2-yl)-6-bromophthalimide収率 87.3%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-Amino-4-iodo-6-bromophthalimide (100 mg, 0.273 mmol) was dissolved in THF (5 mL), and the solution was added with 2-(tributylstannyl)thiophene (0.173 mL, 0.546 mmol) and bis(triphenylphosphine)dichloropalladium (15 mg, 0.022 mmol), followed by stirring under reflux for 12.5 hours under argon atmosphere. The reaction mixture was added with 10% aqueous ammonium fluoride solution, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by slurry using hexane, then purified by preparative thin-layer chromatography (chloroform/acetonitrile=30/1) to obtain 3-amino-4-(thiophen-2-yl)-6-bromophthalimide (77 mg, yield 87%).

後処理

  1. temperatureunder reflux for 12.5 hours under argon atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by slurry
  7. custompurified by preparative thin-layer chromatography (chloroform/acetonitrile=30/1)

出典と根拠

ORDレコード
ord-bd1d487b26d04c6bb41832b318163851
出典データセット
uspto-grants-2010_06
特許番号
US07745641B2

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