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

HRID 12199

반응식

HRID 12199 반응식
[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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole2회

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-831366161355451eb87675e81341adfa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727985B2

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