Triethylamine → 1-Phenylsulfonyl-5-trimethylsilylethynylindole

HRID 352768ノート

反応式

HRID 352768 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH3:46][Si:47]([C:50]#[CH:51])([CH3:49])[CH3:48]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C.CN(C)C=O>[C:14]1([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:51]#[C:50][Si:47]([CH3:49])([CH3:48])[CH3:46])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

10

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indole

生成物 1

HCID 227101661-Phenylsulfonyl-5-trimethylsilylethynylindole

試薬・触媒・溶媒 5

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In tetrahydrofuran (7.00 ml), 5-bromo-1-phenylsulfonylindole (1.50 g) and triphenylphosphine (351 mg) were dissolved. Triethylamine (20 ml), N,N-dimethylformamide (7.00 ml), trimethylsilylacetylene (945 up) and palladium acetate (100 mg) were added to the resulting solution at room temperature, followed by heating under reflux for 5 hours. After the reaction mixture was allowed to cool down to room temperature, ethyl acetate and water were added to the reaction mixture to separate the organic layer. The resulting organic layer was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%) was obtained as a white solid.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customto separate the organic layer
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=20:1 to 10:1), whereby the title compound (935 mg, 59%)
  8. customwas obtained as a white solid

出典と根拠

ORDレコード
ord-fcfe8dd1bb1e435ab49ee672503ac59c
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

反応ノート

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