Dimethyl Sulfoxide → 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

HRID 1768019노트

반응식

HRID 1768019 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][CH2:11]I)[C:6]=2[CH:13]=1.N1CC=C([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)CC1.C([N:32]([CH2:36][CH3:37])[CH:33]([CH3:35])C)(C)C.[CH3:38]S(C)=O>>[S:9]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:13][C:6]=2[C:7]([CH2:10][CH2:11][N:32]2[CH2:33][CH:35]=[C:38]([C:22]3[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:20][CH:21]=3)[CH2:37][CH2:36]2)=[CH:8]1

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 236144415-Chloro-3-(2-iodoethyl)-1-benzothiophene

생성물 1

HCID 112336643-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

실험 절차

A mixture of 2-(5-chloro-1-benzothiophene-3-yl)ethyl iodide (318 mg. 1 mmol) (obtained by the above mentioned process) and 3 (1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (198 mg, 1 mmol) was heated at 120° C. in DMSO in the presence of N,N-diisopropylethylamine (5 ml, excess) for 24 hrs. At the end, the reaction mixture was quenched with water and extracted with chloroform. The organic layer was washed with water and dried over anhydrous MgSO4 and concentrated to dryness. The dark colored solid was purified by silica-gel column chromatography by eluting it with 70% ethyl acetate:hexane. 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole was isolated as yellow oil; Yield: 115 mg (29%); 393 (M+H); 1H-NMR: δ 8.10(1H, s, NH), 7.91(1H, d, J=8 Hz), 7.77(2H, m), 7.25(6H, m), 6.24(1H, s), 3,37(2H, d, J=3 Hz), 3.18(2H, t, J=7.7 Hz), 2.87(4H, m), 2.68(2H, s).

후처리

  1. customobtained by the
  2. customAt the end, the reaction mixture was quenched with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated to dryness
  7. customThe dark colored solid was purified by silica-gel column chromatography
  8. washby eluting it with 70% ethyl acetate

출처 및 근거

ORD 기록
ord-bbff77031d474f3a8a7fb2e02242f78c
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235569B2

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