Boric Acid → 5-phenyl-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine

반응식

Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=1.B(O)(O)O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[C:18]1([C:2]2[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]3[CH2:14][CH2:13][CH2:12][N:11]3[S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:21]=[CH:20][CH:19]=1

참가 물질

실험 절차

5-bromo-3-(1-tosyl-2-(S)-pyrrolidinylmethoxy)pyridine from step 51b (300 mg, 10.73 mmol), boric acid (107 mg, 10.88 mmol) and Pd(0) (26 mg) were mixed together in benzene (2 mL), and the mixture was heated at reflux for 16 hours. NaHCO3 solution (2%, 1 mL) was added, and the mixture was extracted with chloroform. The CHCl3 was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane 1:1 to afford the title compound (300 mg).