4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole → 6-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene
Reaction equation
[CH2:1]([C:4]1([CH3:29])[C:9]2[N:10]([CH2:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH2:20])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7][N:6]([CH3:28])[CH2:5]1)C=C>CO.Cl[Pd]Cl>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH:19]2[CH2:20][CH2:1][C:4]3([CH3:29])[CH2:5][N:6]([CH3:28])[CH2:7][C:8]4[C:16]5[CH:15]=[C:14]([CH3:17])[CH:13]=[CH:12][C:11]=5[N:10]([C:9]=43)[CH2:18]2)=[CH:22][CH:23]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (50 mg, 0.138 mmol) in MeOH (3 mL) was added PdCl2 (25 mg, 0.14 mmol). Hydrogen gas was purged through the solution for 1 h. The reaction mixture was filtered through Celite bed and the Celite bed was rinsed with MeOH. The filtrate was concentrated under reduced pressure and the residue was purified by reverse HPLC to obtain 6-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene. 1H NMR (Freebase, CDCl3) δ (ppm): 6.18-7.21 (m, 2H), 6.9-7.1 (m, 4H), 6.8 (m, 1H), 5.0 (d, 2H), 3.96 (d, 2H), 3.1 (d, 2H), 2.62 (m, 1H), 2.56 (s, 3H), 2.38 (s, 3H), 2.3 (m, 2H), 1.65 (m, 2H), 1.42 (s, 3H).