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

HRID 504743노트

반응식

HRID 504743 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b986040bc8214caca0fced403f3773f7
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777047B2

반응 노트

불러오는 중…