1-Bromo-3-[(trifluoromethyl)thio]benzene

To a mixture of compound 141-1 (0.03 g, 0.11 mmol, 1 eq) and compound 141-la (1601) (34.7 mg, 0.13 mmol, 1.2 eq) in dioxane (2 mL) was added Pd2(dba)3 (10.3 mg, 0.01 mmol, 0.1 eq), XPhos (10.7 mg, 0.02 mmol, 0.2 eq) and K2C03 (46.7 mg, 0.33 mmol, 3 eq) under N2. The mixture was stirred for 10 h at 100C. LCMS showed the reaction was complete. The mixture was quenched by EA (30 mL), and the mixture was filtered and the filtered cake was washed with EA (20 mL*3). The combined organic phase was washed with brine (20 mL*3), dried with anhydrous Na2SC>4, filtered and concentrated in vacuum. The residue was purified by pre-HPLC was obtained. LCMS (ESI): RT = 0.662 min, mass calc. for: C18H17F3N4O2S2 442.07, m/z found 442.9 [M+H]+; lH NMR (400 MHz, CD3OD) delta 9.01 (s, 1H), 7.92 - 7.79 (m, 3H), 7.55 - 7.42 (m, 3H), 7.38 - 7.33 (m, 2H), 3.99 (s, 3H), 2.60 - 2.57 (m, 3H).General procedure: A microwave vial (5 mL) was sealed under inert atmosphere (ArGlovebox) with a stir bar, Selectfluor (177.1 mg, 0.5 mmol, 2 equiv), silver trifluoromethanesulfonate (12.8 mg, 0.05 mmol, 20 mol%) andarylmercaptodifluoroacetic acids (0.25 mmol, 1.0 equiv). To this vial, DCM (1.8 mL) and trifluoroacetic acid (76.5 muL, 1.0 mmol, 4.0 eq.) aswell as water (0.2 mL) were added and the mixture was heated for90 min at 55 C. The resulting mixture was cooled down to room temperature, diluted with dichloromethane (4 mL), washed with water(3 ×5 mL) and brine (5 mL), dried over anhydrous MgSO4 and filtered.The resulting extract was concentrated in a rotary evaporator. The resultingcrude product was dissolved in a small quantity of dichloromethaneand loaded on to a silica cartridge (10 g, Biotage), airdried and eluted with pentane. The pure fractions were combined andsolvent evaporated to obtain the pure products.

Molecular Weight:257.07
XLogP3:4.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:255.91692
Monoisotopic Mass:255.91692
Topological Polar Surface Area:25.3
Heavy Atom Count:12
Complexity:148
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes