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

HRID 746611ノート

反応式

HRID 746611 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-706b3f1ab12142ec846fb90f6e0df641
出典データセット
uspto-grants-2008_07
特許番号
US07393865B2

反応ノート

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