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

HRID 746611Notes

Reaction equation

HRID 746611 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1)(O)[CH3:15].CS(O)(=O)=O.[NH4+].[OH-]>C(Cl)Cl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]([C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[S:9][C:5]=2[CH2:4][CH2:3][N:2]([CH3:1])[CH3:24])=[CH2:15])=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic Acid2×HCID 14923Ammonium HydroxideHCID 116817141-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol

Product 1

HCID 11716841(2-{3-[1-(5-Fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amineYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol in (1.65 g, 4.79 mmol) in methylene chloride (30 mL) at room temperature, methanesulfonic acid (310 uL, 4.8 mol) was added dropwise and the reaction was allowed to stir for 2 hours. Additional methanesulfonic acid (3.1 mL, 47.9 mmol) was added and the reaction was stirred for 2 more hours. The reaction was neutralized with aq NH4OH and was extracted with methylene chloride. Organic layer was concentrated. The reaction mixture was chromatographed on silica gel with 9:1 DCM:MeOH as eluent to afford 923 mg of (2-{3-[1-(5-fluoro-pyridin-2-yl)-vinyl]-benzo[b]thiophen-2-yl}-ethyl)-dimethyl-amine (Compound 7-2) (59%).

Workup

  1. stirringthe reaction was stirred for 2 more hours
  2. extractionwas extracted with methylene chloride
  3. concentrationOrganic layer was concentrated
  4. customThe reaction mixture was chromatographed on silica gel with 9:1 DCM

Sources & evidence

ORD record
ord-706b3f1ab12142ec846fb90f6e0df641
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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