Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[C:13]1([CH3:26])[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2([C:24]#N)[CH2:23][CH2:22][CH2:21][O:20]2)[CH:14]=1.[OH:27]S(O)(=O)=O>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:24]([C:19]1([C:15]2[CH:14]=[C:13]([CH3:26])[CH:18]=[CH:17][CH:16]=2)[CH2:23][CH2:22][CH2:21][O:20]1)=[O:27]To a solution of 2-bromopyridine (418 mg, 2.65 mmol) in THF (10 mL) was added n-BuLi (1.65 mL, 2.65 mmol, 1.6 N in hexane) at −78° C. After 15 mins, a solution of Example 91C (4.45 mg, 1.76 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for 15 minutes and 2 mL of 1 M H2SO4 was added slowly. Then the mixture was heated at 50° C.-60° C. for 30 minutes. After cooling to room temperature, the aqueous phase was separated and extracted with ethyl acetate (15 mL×3). The combined organic phases was washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to provide the title compound. LC-MS: m/z (M+H): 268.
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