Potassium Carbonate → 5-(5-Phenyl-1,3,4-thiadiazol-2-yl)indolin-2-one

HRID 588262ノート

反応式

HRID 588262 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12]3)O1.Br[C:21]1[S:22][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:24][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[C:26]1([C:23]2[S:22][C:21]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[NH:14][C:13](=[O:18])[CH2:12]4)=[N:25][N:24]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 131041172-Bromo-5-phenyl-1,3,4-thiadiazoleHCID 219314865-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

生成物 1

HCID 904174015-(5-Phenyl-1,3,4-thiadiazol-2-yl)indolin-2-one収率 25.1%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (98 mg, 0.38 mmol) in dioxane (0.76 ml) was added PdCl2(dppf) CH2Cl2 (28 mg, 0.039 mmol), 2-bromo-5-phenyl-1,3,4-thiadiazole (138 mg, 0.57 mmol) and 2 M potassium carbonate (aq, 568 μL). The mixture was stirred at 90° C. for 4 hour. The residue was extracted with EtOAc, and the organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc) to give 5-(5-phenyl-1,3,4-thiadiazol-2-yl)indolin-2-one (28 mg) as brown oil.

後処理

  1. extractionThe residue was extracted with EtOAc
  2. washthe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (n-hexane/EtOAc)

出典と根拠

ORDレコード
ord-9d35228f579f4fb8b2f021759a2a4308
出典データセット
uspto-grants-2016_01
特許番号
US09227962B2

反応ノート

読み込み中…