HCID 45375942, compound → HCID 59455096, compound

HRID 1400404Notes

Reaction equation

HRID 1400404 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[C:12](/[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)\[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1>CO.[Pd]>[F:20][C:17]1[CH:18]=[CH:19][C:14](/[C:12](/[CH3:13])=[CH:11]/[N:7]2[C:8]3[CH:9]=[CH:10][CH:2]=[CH:3][C:4]=3[C:5]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][C:6]2=3)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 45375942HCID 45375942, compound

Product 1

HCID 59455096HCID 59455096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-8-Chloro-5-(2-(4-fluorophenyl)prop-1-enyl)-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.200 g) was dissolved in MeOH which was hydrogenated over 10% Pd—C at 40° C. and 30 bars H2. The progress of reaction was monitored by TLC. The solvent was evaporated and the residue was purified by HPLC. 1H NMR (CDCl3, TFA salt) δ (ppm): 7.58 (m, 2H), 7.42 (m, 1H), 7.25 (m, 3H), 7.15 (m, 2H), 6.80 (s, 1H), 4.80 (m, 1H), 4.20 (m, 1H), 3.90 (m, 1H), 3.35 (m, 2H), 3.05 (s, 3H), 2.90 (m, 1H), 1.95 (s, 3H).

Workup

  1. customThe progress of reaction
  2. customThe solvent was evaporated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-ebf3a18d910148ba85968ca658a1abbf
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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