2-Thiophenesulfonyl chloride → HCID 57901653、化合物

HRID 1851489ノート

反応式

HRID 1851489 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH3:17])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:23]([C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)(=[O:25])=[O:24])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

参加物

4

反応物 2

HCID 855182-Thiophenesulfonyl chlorideHCID 15399415ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate

生成物 1

HCID 57901653HCID 57901653、化合物収率 57%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mixed solution of ethyl 7-amino-5-methoxy-1H-indole-2-carboxylate (0.40 g) and pyridine (10 mL) was added 2-thiophenesulfonyl chloride (0.38 g) under ice-cooling, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=15:85-35:65), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (370 mg, yield 57%) as colorless needle crystals. melting point 158-159° C.

後処理

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crystals were recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-a12c6b160168497292c4616d56dae2e8
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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