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

HRID 576522Notes

Reaction equation

HRID 576522 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]=1

Participants

4

Reactant 1

HCID 673564374-allyl-5-[2-(4-fluoro-phenyl)-allyl]-2,4,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 533781656-(4-Fluoro-phenyl)-2,3a,10-trimethyl-1,2,3,3a,4,5,6,7-octahydro-2,7a-diaza-cyclohepta[jk]fluorene

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

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).

Workup

  1. customHydrogen gas was purged through the solution for 1 h
  2. filtrationThe reaction mixture was filtered through Celite bed
  3. washthe Celite bed was rinsed with MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by reverse HPLC

Sources & evidence

ORD record
ord-599b3ba4d1784231a8473cb89f306ed5
Source dataset
uspto-grants-2015_05
Patent number
US09040519B2

Reaction notes

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