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,4,7-hexahydro-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>C(Cl)Cl>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[CH2:18][N:10]3[C:11]4[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=4[C:8]4[CH2:7][N:6]([CH3:28])[CH2:5][C:4]([CH3:1])([CH2:29][CH:20]=2)[C:9]3=4)=[CH:26][CH:25]=1Participants
Procedure
To a solution of the 4-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 0.64 mmol) in degassed DCM (7 mL) was added dropwise a solution of Grubbs'2nd generation catalyst (27.61 mg, 0.0325 mmol, 5 mol %) in degassed DCM (3 mL) under an nitrogen atmosphere. The resultant solution was heated at 115° C. for 1 h in a microwave. The solvent was evaporated in vacuo and the residue was purified by reverse HPLC to obtain 6-(4-fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,7-hexahydro-2,7a-diaza-cyclohepta[jk]fluorene as an off white solid (50 mg). 1H NMR (Freebase, CDCl3) δ (ppm): 7.40 (m, 2H), 7.30 (d, 1H), 7.10 (d, 1H), 7.04-6.98 (m, 2H), 5.99 (d, 1H), 4.96 (d, 1H), 3.99 (d, 1H), 3.96 (s, 2H), 2.70 (d, 2H), 2.55 (s, 3H), 2.42 (s, 3H), 2.30 (d, 1H), 2.21 (m, 1H), 1.50 (s, 3H).
Workup
- customThe solvent was evaporated in vacuo
- customthe residue was purified by reverse HPLC
Sources & evidence
- ORD record
- ord-9dce8bca943341e29af8f9b31c7531ef
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040519B2
Reaction notes
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