Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([O:13][CH3:14])=[O:12])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.C(SC1C(C(OC)=O)=C(C(F)(F)F)C=C(SCC)N=1)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>CC#N.O.CCOC(C)=O>[CH2:9]([S:8][C:6]1[C:5]([C:11]([O:13][CH3:14])=[O:12])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=[C:2]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[N:7]=1)[CH3:10]
A solution of 2 g of a ˜1:1 mixture of methyl 6-chloro-2-(ethylsulfanyl)-4-(trifluoromethyl)-pyridine-3-carboxylate and methyl 2,6-bis(ethylsulfanyl)-4-(trifluoromethyl)-pyridine-3-carboxylate, 1.7 ml (20.0 mmol) morpholine and 3.5 ml (20.0 mmol) DIPEA in MeCN (10 ml) was heated in the microwave to 150° C. for 4 h. The RM was then diluted with water and EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 440 mg (1.3 mmol, 16% over 2 steps) methyl 2-(ethylsulfanyl)-6-morpholin-4-yl-4-(trifluoromethyl)-pyridine-3-carboxylate.
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