2-Thiophenesulfonyl chloride → ethyl 7-[(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylate

HRID 504743ノート

反応式

HRID 504743 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][C:17]([F:20])([F:19])[F:18])[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:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1>[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[S:26]([NH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]([F:20])([F:18])[F:19])[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)(=[O:28])=[O:27]

参加物

4

反応物 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57476183ethyl 7-amino-5-(trifluoromethoxy)-1H-indole-2-carboxylate

生成物 1

HCID 57476185ethyl 7-[(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylate収率 89.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mixture of ethyl 7-amino-5-(trifluoromethoxy)-1H-indole-2-carboxylate (2.53 g) and pyridine (50 mL) was added thiophene-2-sulfonyl chloride (1.94 g) at 0° C., and the mixture was stirred at room temperature for 4 hr, and concentrated. 1N Hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained crystals were washed with diisopropyl ether to give the title compound (3.40 g, yield 89%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point 196-197° C.

後処理

  1. concentrationconcentrated
  2. addition1N Hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washThe obtained crystals were washed with diisopropyl ether

出典と根拠

ORDレコード
ord-b986040bc8214caca0fced403f3773f7
出典データセット
uspto-grants-2010_08
特許番号
US07777047B2

反応ノート

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