Water → 5-Chloro-1-methylindole

HRID 1017583

반응식

HRID 1017583 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[OH-].[K+].I[CH3:14].O>CN(C=O)C>[CH3:14][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 871105-Chloroindole

생성물 1

HCID 108558435-Chloro-1-methylindole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To room temperature solution of 5-chloroindole (4.97 g) in dry DMF (40 mL) was added potassium hydroxide pellets (2.76 g) and stirred 1 h until most of the solid dissolved. The resulting mixture was cooled to 0° C. in an ice bath and iodomethane (2.45 mL) was added dropwise and later stirred overnight at room temperature under argon. The reaction mixture was poured into water and extracted twice with ETOAc. The combined ETOAc portions were combined, washed with water, dried over magnesium sulfate, concentrated, and flash chromatographed with 10% ETOAc/Hexane to give 1-methyl-5-chloroindole as a pink liquid (5.43 g).

후처리

  1. dissolutiondissolved
  2. extractionextracted twice with ETOAc
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customflash chromatographed with 10% ETOAc/Hexane

출처 및 근거

ORD 기록
ord-f764d5d4ae964da5a8d063545527fe57
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479490B2

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