5-(2-Bromoethyl)-2,3-dihydro-1-benzofuran → HCID 44516993, compound

HRID 2192349Notes

Reaction equation

HRID 2192349 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.Br[CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]2[O:35][CH2:34][CH2:33][C:32]=2[CH:36]=1>C(#N)C>[CH:10]([O-:11])=[O:9].[O:35]1[C:31]2[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][N+:1]34[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]3)[C@@H:3]([O:9][C:10]([C:12]3([C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])[CH2:2]4)=[CH:36][C:32]=2[CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 218311605-(2-Bromoethyl)-2,3-dihydro-1-benzofuranHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 44516993HCID 44516993, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (126 mg) and 5-(2-bromo-ethyl)-2,3-dihydro-benzofuran (105 mg, 0.46 mmol) in acetonitrile (1.5 mL) was stirred at room temperature for 22 h. The volatiles were evaporated and the residue purified by silica gel chromatography eluting with dichloromethane then 5% then 10% MeOH/dichloromethane. The relevant fractions were combined and evaporated and the residue triturated with dichloromethane to give an off -white foam. Further purification was achieved by reverse-phase HPLC (5-98% MeCN containing 0.1% formic acid) to give the title compound (70 mg) as a white gummy solid.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue purified by silica gel chromatography
  3. washeluting with dichloromethane
  4. customevaporated
  5. customthe residue triturated with dichloromethane
  6. customto give an off -white foam
  7. customFurther purification

Sources & evidence

ORD record
ord-a0d50768ca8f48daa3a97b30c2b1bd21
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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