Potassium Iodide → 2-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

HRID 2356387

반응식

HRID 2356387 반응식
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2].Br[CH2:20][CH2:21][CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH:12]1[CH2:17][CH2:16][N:15]([CH2:20][CH2:21][CH2:22][S:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH2:14][CH2:13]1)=[CH:9][CH:8]=[C:7]([F:18])[CH:6]=2)[CH3:2]

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14575314Benzene, 1-[(3-bromopropyl)thio]-4-fluoro-HCID 577188362-Ethyl-6-fluoro-3-piperidin-4-yl-1H-indole

생성물 1

HCID 577188372-Ethyl-6-fluoro-3-{1-[3-(4-fluoro-phenylsulfanyl)-propyl]-piperidin-4-yl}-1H-indole

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-ethyl-6-fluoro-3-piperidin-4-yl-1H-indole (0.9 g), 1-(3-Bromo-propylsulfanyl)-4-fluoro-benzene (1.0 g), potassium iodide (20 mg) and potassium carbonate (0.7 g) in DMF (10 ml) is heated at 100° C. for 3 h, and allowed to cool to rt overnight. Ethyl acetate (50 ml) and water (25 ml) are added and the organic phase is washed with water, dried and concentrated in vacuo. The crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt is prepared by reaction in acetone with the appropriate amount of ethereal HCl giving, after recrystallisation from ether, 1.1 g pure product (70%) as white crystals.

후처리

  1. temperatureto cool to rt overnight
  2. washthe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography (95:5 CH2Cl2:MeOH) and its hydrochloride salt
  6. customis prepared by reaction in acetone with the appropriate amount of ethereal HCl giving
  7. customafter recrystallisation from ether, 1.1 g pure product (70%) as white crystals

출처 및 근거

ORD 기록
ord-81d413e111dd46c4a5cd7d679dfd1885
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759365B2

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