Trifluoroacetic acid → HCID 11530223, compound

HRID 746617Notes

Reaction equation

HRID 746617 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[N:15]=[C:14]([C:16]([C:18]2[C:19]3[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=3[S:21][C:22]=2[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])=[CH2:17])[CH:13]=[CH:12][CH:11]=1>CO.[Pd]>[CH3:8][O:9][C:10]1[N:15]=[C:14]([CH:16]([C:18]2[C:19]3[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=3[S:21][C:22]=2[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH3:17])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11559143HCID 11559143, compound

Product 1

HCID 11530223HCID 11530223, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The TFA salt of (2-{3-[1-(6-methoxy-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (190 mg, mmol) was dissolved in MeOH (12 mL) and a catalytic amount of 10% Pd/C was added. The reaction was stirred under 1 Atm of H2 for 2.5 hours, filtered over celite, washed with dichloromethane, concentrated in vacuo and purified by mass triggered preparative HPLC to give (2-{3-[1-(6-methoxy-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 15-2). MH+=341.0, tR=5.2 min.

Workup

  1. filtrationfiltered over celite
  2. washwashed with dichloromethane
  3. concentrationconcentrated in vacuo
  4. custompurified by mass

Sources & evidence

ORD record
ord-873663cdf5224d13bd5983999d6af8db
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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