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0 °C

To a suspension of 3-chloro-4-(3,3,3-trifluoro-2-hydroxy-1-methyl-2-quinolin-3-yl-propyl)-phenol (Example 179, 75 mg) in N,N-dimethylacetamide (1 ml) was added NaH (60% dispersion in mineral oil, 9 mg) at 0° C. The mixture was stirred at 0° C. for 1 h and at room temperature for 1 h. 4-Methylsulfonylbenzyl bromide (54 mg) was added and the mixture was stirred at room temperature for 3 h. Cesium carbonate (32 mg) was added and the mixture was stirred for 2 days at room temperature and for 5 h at 50° C. The reaction mixture was poured into water and extracted with EtOAc. The organic phase was washed with brine and dried (MgSO4). The product was purified by chromatography (SiO2, cyclohexane=>cyclohexane/EtOAc 1:1) to give the title compound (69 mg) as a light yellow solid. MS (m/e)=550.3 [M+H+].

1. stirringthe mixture was stirred at room temperature for 3 h
2. stirringthe mixture was stirred for 2 days at room temperature and for 5 h at 50° C
3. extractionextracted with EtOAc
4. washThe organic phase was washed with brine
5. dry with materialdried (MgSO4)
6. customThe product was purified by chromatography (SiO2, cyclohexane=>cyclohexane/EtOAc 1:1)