Hydrogen Bromide → 2-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

HRID 730030Notes

Reaction equation

HRID 730030 reaction equation
[Na].C([CH:4]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:6])#N.Br>C(O)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:4][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[O:6])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 5360545SodiumHCID 141952232-(4-Fluorophenyl)-3-oxo-3-(pyridin-4-yl)propanenitrile

Product 1

HCID 110421332-(4-Fluorophenyl)-1-(pyridin-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting materials are converted in a condensation reaction with the aid of metallic sodium in an alcohol, for example ethanol, into 2-cyano-2-(4-fluorophenyl)-1-(4-pyridyl)ethanone (IIIa). The cyano group is then removed by hydrolysis, for example with hydrobromic acid, and decarboxylation, giving 2-(4-fluorophenyl)-1-(4-pyridyl)ethanone (IVa). In the next step, IVa is converted by treatment with ammonium chloride/sodium acetate in an alcoholic solvent, such as methanol, into the oxime (Va). By reaction with p-toluenesulfonyl chloride in pyridine, the latter is converted into the tosylate (VIa). From the tosylate, the thione compound (IIa) is obtained by treatment with sodium ethoxide and reaction of the azirene intermediate formed with potassium thiocyanate.

Sources & evidence

ORD record
ord-2bd726022bd74dbaa4a632833e648058
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

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