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

HRID 1768019ノート

反応式

HRID 1768019 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bbff77031d474f3a8a7fb2e02242f78c
出典データセット
uspto-grants-2007_06
特許番号
US07235569B2

反応ノート

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