Dimethyl Sulfoxide → 3-(1-(2-(7-methoxybenzofuran-3-yl)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

HRID 1768007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768007
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13]I)[C:7]=2[CH:6]=[CH:5][CH:4]=1.N1CC=C([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22]2)CC1.C([N:33]([CH2:37][CH3:38])[CH:34]([CH3:36])C)(C)C.[CH3:39]S(C)=O>>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][N:33]3[CH2:34][CH:36]=[C:39]([C:23]4[C:24]5[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=5)[NH:21][CH:22]=4)[CH2:38][CH2:37]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082HCID 23001082, VerbindungHCID 236144473-(2-Iodoethyl)-7-methoxy-1-benzofuran

Produkt 1

HCID 112802073-(1-(2-(7-methoxybenzofuran-3-yl)ethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Versuchsvorschrift

A mixture of 2-(7-methoxy-1-benzofuran-3-yl)ethyl iodide (301 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-(7-methoxy-1-benzofuran-3-yl)ethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole was isolated as yellow solid. mp 156° C.; Yield: 80 mg (21%); 373 (M+H); 1H NMR: δ 8.4 (bs, 1H), 7.9 (d,1H), 7.5 (s, 1H), 7.35–6.80 (m, 7H), 6.2 (m,1H), 3.97 (s, 3H), 3.50 (m,2H), 3.19 (m, 2H), 2.93 (m, 4H), 2.67 (m, 2H).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-78b621894beb4e24a442e4b8893e7252
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235569B2

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