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

HRID 746611노트

반응식

HRID 746611 반응식
[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

참가 물질

5

반응물 3

HCID 6395Methanesulfonic Acid2회HCID 14923Ammonium HydroxideHCID 116817141-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-1-(5-fluoro-pyridin-2-yl)-ethanol

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-706b3f1ab12142ec846fb90f6e0df641
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393865B2

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