4-Hydroxydiphenylmethane (I) is condensed with tert-butyl bromoacetate (II) in the presence of NaH and Bu-4NI to form the aryloxyacetate adduct (III). Ester group reduction in (III) employing LiAlH4 provides alcohol (IV), which is further treated with p-toluenesulfonyl chloride in pyridine, yielding tosylate (V) (1,2). Finally, condensation of tosylate (V) with ethyl isonipecotate (VI) furnishes the title compound (1-3).

Alkylation of 4-hydroxydiphenylmethane (I) with tert-butyl bromoacetate (II) in the presence of NaH and Bu4NI in DMF affords ether (III). The ester function of (III) is then reduced by LiAlH4 to furnish the primary alcohol (IV), which is subsequently activated as the corresponding tosylate (V) (1,2). Condensation of tosylate (V) with 5-azabenzimidazole (VI) gives rise to a mixture of the three possible regioisomers (VII), (VIII) and (IX), which can be separated by means of flash chromatography. The desired isomer (IX) is then converted to the N-oxide (X) employing m-chloroperbenzoic acid in CHCl3 (1-3). Finally, reaction of N-oxide (X) with cyanotrimethylsilane produces the target nitrile (3).

4-Hydroxydiphenylmethane (I) is condensed with tert-butyl bromoacetate (II) in the presence of NaH and Bu-4NI to form the aryloxyacetate adduct (III). Ester group reduction in (III) employing LiAlH4 provides alcohol (IV), which is further treated with p-toluenesulfonyl chloride in pyridine, yielding tosylate (V) (1,2). Finally, condensation of tosylate (V) with ethyl isonipecotate (VI) furnishes the title compound (1-3).

Alkylation of 4-hydroxydiphenylmethane (I) with tert-butyl bromoacetate (II) in the presence of NaH and Bu4NI in DMF affords ether (III). The ester function of (III) is then reduced by LiAlH4 to furnish the primary alcohol (IV), which is subsequently activated as the corresponding tosylate (V) (1,2). Condensation of tosylate (V) with 5-azabenzimidazole (VI) gives rise to a mixture of the three possible regioisomers (VII), (VIII) and (IX), which can be separated by means of flash chromatography. The desired isomer (IX) is then converted to the N-oxide (X) employing m-chloroperbenzoic acid in CHCl3 (1-3). Finally, reaction of N-oxide (X) with cyanotrimethylsilane produces the target nitrile (3).

Alkylation of 4-hydroxydiphenylmethane (I) with tert-butyl bromoacetate (II) in the presence of NaH and Bu4NI in DMF affords ether (III). The ester function of (III) is then reduced by LiAlH4 to furnish the primary alcohol (IV), which is subsequently activated as the corresponding tosylate (V) (1,2). Condensation of tosylate (V) with 5-azabenzimidazole (VI) gives rise to a mixture of the three possible regioisomers (VII), (VIII) and (IX), which can be separated by means of flash chromatography. The desired isomer (IX) is then converted to the N-oxide (X) employing m-chloroperbenzoic acid in CHCl3 (1-3). Finally, reaction of N-oxide (X) with cyanotrimethylsilane produces the target nitrile (3).