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

HRID 1768025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1768025
I[CH2:2][CH2:3][C:4]1[C:5]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:6]=2[O:7][CH:8]=1.N1CC=C([N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)CC1.C([N:35]([CH2:39][CH3:40])[CH:36]([CH3:38])C)(C)C.[CH3:41]S(C)=O>>[O:7]1[CH:8]=[C:4]([CH2:3][CH2:2][N:35]2[CH2:36][CH:38]=[C:41]([C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[NH:23][CH:24]=3)[CH2:40][CH2:39]2)[C:5]2[CH:16]=[CH:15][C:14]3[C:9]([C:6]1=2)=[CH:10][CH:11]=[CH:12][CH:13]=3

Komponenten

5

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 23001082(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 236144513-(2-Iodo-ethyl)-naphtho[1,2-b]furan

Produkt 1

HCID 236144503-{1-(2-naphtho[1,2-b]furan-3-yl-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole

Versuchsvorschrift

A mixture of 3-(2-iodo-ethyl)-naphtho[1,2-b]furan (321 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-naphtho[1,2-b]furan-3-yl-ethyl)-1,2,3,6-tetrahydro-4-pyridinyl}-1H-indole was isolated as yellow solid. Yield: 120 mg (30%); 393 (M+H).

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 acetate

Quellen und Nachweise

ORD-Eintrag
ord-71d34400063241b78d77037b8deec5e5
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235569B2

Notizen zur Reaktion

Wird geladen…