[CH2:1]([OH:3])[CH3:2].CN([CH:7]=[O:8])C.C(P(C1C=CC=CC=1)C1C=CC=CC=1)CCP(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)S(O[C:44]1[CH:45]=[N:46][CH:47]=[C:48]([Cl:50])[CH:49]=1)(=O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCN(CC)CC>[Cl:50][C:48]1[CH:47]=[N:46][CH:45]=[C:44]([CH:49]=1)[C:7]([O:3][CH2:1][CH3:2])=[O:8]
To ethanol (66 mL) and DMF (66 mL) was added Et3N (29.4 mL), 1,3-propanediylbis(diphenylphosphine) (3.48 g) and palladium acetate (1.9 g) in ice-water bath. To this was added 5-chloro-3-pyridinyl trifluoromethanesulfonate (22.1 g) at the temperature. The mixture was stirred at 50° C. for 4 hours under CO (1 atom). The mixture was partitioned betwwen EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water three times, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography (silica gel, 200 mL) eluted with hexane-EtOAc=15-1 and 10-1 to give ethyl 5-chloronicotinate (10.5 g) as a pale brown oil.
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