Cl[C:2]1[N:17]=[CH:16][C:15]([F:18])=[CH:14][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1)=[O:5].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][C:21]=1[S:27][CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[N:17]=[CH:16][C:15]([F:18])=[CH:14][C:3]=2[C:4]([NH:6][C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)=[O:5])=[CH:22][C:21]=1[S:27][CH3:28]2-Chloro-5-fluoro-N-(trans-4-hydroxycyclohexyl)nicotinamide (150 mg, 0.55 mmol) was added to a solution of 4-chloro-3-(methylsulfanyl)phenol (96 mg, 0.55 mmol), caesium carbonate (358 mg, 1.1 mmol) in N,N-dimethylformamide (2 ml). The reaction was stirred under nitrogen at 55° C. for 18 h, cooled, and quenched with 1:1 water:sat. ammonium chloride solution and passed through a chemelute™ cartridge. The solvent. The residue was purified by flash column chromatography using dichloromethane:methanol (100:0 to 96:4) as eluant to afford 2-[4-chloro-3-(methylsulfanyl)phenoxy]-5-fluoro-N-(trans-4-hydroxycyclohexyl)nicotinamide as an amorphous glass (37 mg).
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