Dibutyltin oxide → HCID 178427403、化合物

HRID 520531ノート

反応式

HRID 520531 の反応式
[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

参加物

6

反応物 4

HCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2 回HCID 666940066-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrileHCID 667767806-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile

生成物 1

HCID 178427403HCID 178427403、化合物収率 141.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ab45176c354a4cb48c592a6f228eb966
出典データセット
uspto-grants-2016_05
特許番号
US09326987B2

反応ノート

読み込み中…