Chlorosuccinimide → 3-Chloro-5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indole

HRID 423297노트

반응식

HRID 423297 반응식
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Cl:37])C(=O)C1>C(Cl)Cl>[Cl:37][C:24]1[C:23]2[C:27](=[CH:28][CH:29]=[C:21]([C:18]3[N:17]=[C:16]([C:9]4[S:10][C:11]([C:12]([F:15])([F:14])[F:13])=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=4)[O:20][N:19]=3)[CH:22]=2)[NH:26][CH:25]=1

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

생성물 1

HCID 593183433-Chloro-5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indole수율 16.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

D2 (200 mg) and NCS (65 mg) were dissolved in DCM (5 ml) and stirred overnight at room temperature. The reaction mixture was then partitioned between DCM and H2O. The DCM solution was evaporated to dryness and purified on a Biotage silica cartridge, eluting with a 25-75% mixture of diethyl ether in hexane. This gave the title compound (36 mg) as a brown solid. A second batch of the title compound was also obtained from this purification (86 mg) as a brown solid. δH (CDCl3, 400 MHz): 7.28 (1H, m), 7.45-7.54 (6H, m), 7.93 (1H, s), 8.05 (1H, d), 8.28 (1H, br s), 8.49 (1H, s). MS (ES): C21H11ClF3N3OS requires 445; found 444 (M−H+).

후처리

  1. customThe reaction mixture was then partitioned between DCM and H2O
  2. customThe DCM solution was evaporated to dryness
  3. custompurified on a Biotage silica cartridge
  4. washeluting with a 25-75% mixture of diethyl ether in hexane

출처 및 근거

ORD 기록
ord-41150b8ae4ab410f884a2e746a5d460b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101775B2

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