Dimethylformamide → 6-chloro-7-methylsulfanyl-8-nitro-9H-beta-carboline

HRID 12199

反応式

HRID 12199 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1F)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.CN(C=O)C.[CH3:24][S-:25].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[S:25][CH3:24])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole2 回

生成物 1

HCID 671652196-chloro-7-methylsulfanyl-8-nitro-9H-beta-carboline収率 91.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

A 250 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-β-carboline (Intermediate 5, 3.959 g, 14.9 mmol) and 100 ml anhydrous DMF. The resulting orange mixture was cooled to 0° C. (ice and water bath) and sodium thiomethoxide (1.809 g, 25.8 mmol) in powder form was added slowly thereto. The reaction mixture was stirred for 1 hr at 0° C., warmed to RT, and added slowly to a stirring mixture of 4:1 H2O/saturated aqueous sodium bicarbonate (500 ml). The precipitated solid was collected via suction filtration and air-dried to afford 4.017 g of 6-chloro-7-methylsulfanyl-8-nitro-9H-β-carboline as an orange powder. The crude material was used directly in subsequent steps.

後処理

  1. additionwas added slowly
  2. temperaturewarmed to RT
  3. filtrationThe precipitated solid was collected via suction filtration
  4. customair-dried

出典と根拠

ORDレコード
ord-831366161355451eb87675e81341adfa
出典データセット
uspto-grants-2010_06
特許番号
US07727985B2

関連ノート

読み込み中…