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

HRID 1768014ノート

反応式

HRID 1768014 の反応式
[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

参加物

5

反応物 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 236144373-(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-(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).

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 acetae

出典と根拠

ORDレコード
ord-9c3d517e6e8e4d5caec085b231d0874d
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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