2-Bromo-2'-fluoroacetophenone → HCID 70673754, compound

HRID 1910503Notes

Reaction equation

HRID 1910503 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:10])[CH2:2]2.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])=[O:30]>C(#N)C>[Br-:27].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[F:37])=[O:30])([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 27374492-Bromo-2'-fluoroacetophenoneHCID 70925896Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate

Product 1

HCID 70673754HCID 70673754, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (90 mg, 0.25 mmol, prepared as in example 4) and 2-bromo-1-(2-fluorophenyl)ethanone (65.6 mg, 0.30 mmol) were dissolved in acetonitrile (4 ml) and stirred at room temperature overnight. Acetonitrile was evaporated, and the residue was triturated with Et2O and filtered to obtain 3-((bis(3-fluorophenyl)methoxy)-carbonyl)-1-(2-(2-fluorophenyl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide (51.3 mg, racemic mixture).

Workup

  1. customAcetonitrile was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a4c729a4ab4f4cdeb967881b0fef1e1d
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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