Indole → 1-(3-Chloropropyl)-1H-indole

HRID 1764870노트

반응식

HRID 1764870 반응식
Br[CH2:2][CH2:3][CH2:4][Cl:5].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[OH-].[K+]>CN(C=O)C>[Cl:5][CH2:4][CH2:3][CH2:2][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

참가 물질

5

반응물 3

HCID 798IndoleHCID 80061-Bromo-3-chloropropaneHCID 14797Potassium Hydroxide

생성물 1

HCID 220489601-(3-Chloropropyl)-1H-indole수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
20 °C

실험 절차

To a solution of 1-bromo-3-chloropropane (2.00 g, 12.7 mmol) in DMF (7.0 mL) was added indole (500 mg, 4.24 mmol) followed by powdered KOH (262 mg, 4.66 mmol) at 20° C. The reaction mixture was then stirred for 15 h at 20° C. The reaction was quenched by addition of H2O and the product was extracted with Et2O. The organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. 1-(3-Chloro-1-propyl)indole (580 mg, 71%) was isolated by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a pale yellow oil. 1H NMR (CDCl3, 300 MHz) δ2.28 (qu, 2H, J=6.3 Hz), 3.46 (t, 2H, J=6.2 Hz), 4.36 (t, 2H, J=6.6 Hz), 6.51 (d, 1H, J=3.3 Hz), 7.09-7.18 (m, 2H), 7.20-7.25 (m, 1H), 7.38 (d, 1H, J=8.5 Hz), 7.64 (d, 1H, J=7.7 Hz) ppm.

후처리

  1. customThe reaction was quenched by addition of H2O
  2. extractionthe product was extracted with Et2O
  3. washThe organic solution was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ba1eb35f1598431183df44705ff2353b
출처 데이터셋
uspto-grants-2007_06
특허 번호
USRE039679E1

반응 노트

불러오는 중…