Methyl iodide → 6-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-carbazole
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1.[CH3:15]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 6-bromo-2,3,4,9-tetrahydro-1H-carbazole (1.501 g, 6 mmol) was reacted with k-t-butoxide (0.707 g, 6.3 mmol) and methyl iodide (0.894 g, 6.3 mmol) in DMF (15 ml) to give the desired product (1.443 g, 5.463 mmol, 91%) as an off-white solid, mp 70-73° C. 1H NMR (DMSO-d6) δ 1.73-1.77 (m, 2H), 1.82-1.87 (m, 2H), 2.58 (t, J=6.1 Hz, 2H), 2.70 (t, J=6.1 Hz, 2H), 3.58 (s, 3H), 7.13 (dd, J=1.7, 8.6 Hz, 1H), 7.32 (d, J=8.6 Hz, 1H), 7.55 (d, J=1.5 Hz, 1H); [EI], m/z 263/265 (M)+.