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

HRID 1768014노트

반응식

HRID 1768014 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11]I)=[CH:2]1.N1CC=C([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)CC1.C([N:31]([CH2:35][CH3:36])[CH:32]([CH3:34])C)(C)C.[CH3:37]S(C)=O>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][CH2:11][N:31]2[CH2:32][CH:34]=[C:37]([C:21]3[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:19][CH:20]=3)[CH2:36][CH2:35]2)=[CH:2]1

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 236144373-(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-(1-benzothiophene-3-yl)ethyl iodide (284 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 acetae: hexane. 3-{1-[2-(1-benzothiophene-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole was isolated as yellow solid. mp 195–198° C.; Yield: 180 mg (50%); 359 (M+H); 1HNMR (400 MHz, CDCl3):δ 8.12 (broad s, 1H, NH); 7.92˜6.69 (m, 10H); 6.25˜6.23 (s, 1H); 3.48˜2.60 (m, 10H).

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 acetae

출처 및 근거

ORD 기록
ord-9c3d517e6e8e4d5caec085b231d0874d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235569B2

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