[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC([O-])=O.[Na+].[N:30]#[C:31]Br>CO.C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:31]#[N:30])[CH2:21][CH2:20]3)=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]A solution of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine (346 mg, 1 mmol) in MeOH (20 mL) was treated with NaOAc (574 mg, 7 mmol) then was warmed and stirred for 30 min. The suspension was then treated with a solution of cyanogen bromide (318 mg, 3 mmol) in CH2Cl2 (1.5 mL) at 0° C. The mixture was stirred and allowed to warm to room temperature overnight. The mixture was filtered, washed with MeOH and CH2Cl2, and the material was purified by chromatography on a silica gel column using 0 to 100% CH2Cl2/EtOAc, then 2.5% MeOH/CH2Cl2 to afford (4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarbonitrile (250 mg, 61%).
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