Dimethyl Sulfoxide → 5-Chloro-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

HRID 2173970ノート

反応式

HRID 2173970 の反応式
[Cl:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(N(C(C)C)C(C)C)C.CS(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 86701537(5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

生成物 1

HCID 867015395-Chloro-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of (5-chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol (3.3 g, 9.5 mmol) and N-ethyl-diisopropylamine (8.3 mL, 47.3 mmol) in CH2Cl2 (20 mL)/DMSO (1 mL) was added SO3.Py (4.5 g, 28.4 mmol) at 0° C. The mixture was stirred at 0° C. for 2.5 h, and then stirred at room temperature for 15 h. The reaction was quenched by MeOH. The mixture was stirred for 1 h. The mixture was partially concentrated. The mixture was diluted with H2O, and then the resulted solid was collected by filtration. The resulting residue was triturated with MeOH to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 10.56 (s, 1H), 8.00 (d, J=3.80 Hz, 1H), 7.62 (d, J=3.80 Hz, 1H), 7.60 (d, J=8.60 Hz, 2H), 7.35 (d, J=8.60 Hz, 2H), 7.22 (s, 1H), 2.60 (s, 3H), 2.37 (s, 3H).

後処理

  1. stirringstirred at room temperature for 15 h
  2. customThe reaction was quenched by MeOH
  3. stirringThe mixture was stirred for 1 h
  4. concentrationThe mixture was partially concentrated
  5. additionThe mixture was diluted with H2O
  6. filtrationthe resulted solid was collected by filtration
  7. customThe resulting residue was triturated with MeOH

出典と根拠

ORDレコード
ord-1b97057e36da46349d4921b5ea1ec617
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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