[OH:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[OH-].[K+].[C:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24]Br)[CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].O>CS(C)=O>[Br:8][C:6]1[CH:5]=[CH:4][N:3]([CH2:24][CH:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:19]2)[C:2](=[O:1])[CH:7]=1
To a solution of 2-hydroxy-4-bromopyridine (0.10 g, 0.57 mmol) in DMSO (1.50 mL) was added KOH (0.095 g, 1.70 mmol) and the resulting reaction mixture was stirred for 10 min at room temperature followed by addition of 1-Boc-3-bromomethylpiperidine (0.16 g, 0.57 mmol). The reaction mixture was then stirred at 45° C. for 16 h. After the completion of reaction (TLC monitoring), water was added to the reaction and extracted with EtOAc (3×25 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (100-200 M, 1% MeOH-DCM) to obtain the desired product (0.15 g, 95%). MS: 371.10 (M+H)+.
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