(2-{3-[1-(5-Fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine → (2-{3-[1-(5-Fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine

HRID 746612Notes

Reaction equation

HRID 746612 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=3[S:13][C:14]=2[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=[CH2:9])=[N:6][CH:7]=1>C(O)C.[Pt](=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=3[S:13][C:14]=2[CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 11716841(2-{3-[1-(5-Fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine

Product 1

HCID 11522734(2-{3-[1-(5-Fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-{3-[1-(5-fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (133 mg, 0.407 mmol) in ethanol (7 mL), platinum dioxide (50 mg, 0.2 mmol) was added. Reaction was shaken at 35 psi for 3 hours and at 40 psi for 3 hours under an atmosphere of hydrogen. The reaction mixture was filtered and washed with EtOH. Purification by mass triggered preparative HPLC afforded (2-{3-[1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-3). (MH+=329, tR=40.592, Method 2) The enantiomers (2-{3-[(R)-1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-4) (MH+=329.0, tR=4.617, Method 2) and (2-{3-[(S)-1-(5-fluoro-pyridin-2-yl)-ethyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-5) (MH+=329.0, tR=4.554, Method 2) were separated using a chiral HPLC OJ-H column, Eluent: Hexanes:EtOH=90:10 with 0.1% DEA.

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtOH
  4. customPurification by mass

Sources & evidence

ORD record
ord-b136b94a8a8040f3a7526814e290e634
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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