Dibutyltin oxide → HCID 178427403, 화합물

HRID 520531노트

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HRID 520531 반응식
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:11]=[C:12]([C:28]#[N:29])[C:13]4[CH:14]=[N:15][N:16]([S:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)(=[O:21])=[O:20])[C:17]=4[CH:18]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH:30]1[C:38]2[C:33](=[C:34]([C:39]3[CH:40]=[C:41]([C:58]#[N:59])[C:42]4[CH:43]=[N:44][N:45]([S:48]([C:51]5[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=5)(=[O:50])=[O:49])[C:46]=4[CH:47]=3)[CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1.C[Si]([N:64]=[N+:65]=[N-:66])(C)C.C([Sn](CCCC)=O)CCC>C1(C)C=CC=CC=1>[NH:30]1[C:38]2[C:33](=[C:34]([C:39]3[CH:47]=[C:46]4[C:42]([CH:43]=[N:44][N:45]4[S:48]([C:51]4[CH:56]=[CH:55][C:54]([CH3:57])=[CH:53][CH:52]=4)(=[O:50])=[O:49])=[C:41]([C:58]4[NH:66][N:65]=[N:64][N:59]=4)[CH:40]=3)[CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1.[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[CH:18]=[C:17]4[C:13]([CH:14]=[N:15][N:16]4[S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])=[C:12]([C:28]4[NH:66][N:65]=[N:64][N:29]=4)[CH:11]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

6

반응물 4

HCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2회HCID 666940066-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrileHCID 667767806-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile

생성물 1

HCID 178427403HCID 178427403, 화합물수율 141.3%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

6-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile (0.669 g, 1.679 mmol) and 6-(1H-indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile (0.561 g, 1.360 mmol) were slurried in toluene (60 ml) and treated with trimethylsilyl azide (0.887 ml, 6.68 mmol) and dibutyl(oxo)stannane (0.151 g, 0.608 mmol). The reaction mixture was heated, under nitrogen at 120° C. for 16 h, then additional trimethylsilyl azide (0.221 ml, 1.67 mmol) was added. After heating for a further 2 h, the solution was evaporated to dryness, treated with methanol (30 ml) and absorbed onto Florisil. The Florisil was loaded onto a silica cartridge (100 g) which was eluted with 0-30% methanol+1% triethylamine/dichloromethane. The appropriate fractions were combined and concentrated to give the title compound as a brown solid (1.724 g).

후처리

  1. temperatureAfter heating for a further 2 h
  2. customthe solution was evaporated to dryness
  3. additiontreated with methanol (30 ml)
  4. customabsorbed onto Florisil
  5. washwas eluted with 0-30% methanol+1% triethylamine/dichloromethane
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ab45176c354a4cb48c592a6f228eb966
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326987B2

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