2-CHLORO-4-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE

General procedure: To a solution of 1 (0.5 mmol) and pyridine (1.5 mL) in THF (3 mL)was added 2 (0.75 mmol) slowly at 25 C. After the complete consumption of 1 (as monitored by TLC), the reaction was quenched by the addition of 2 N HCl (5 mL) and then extracted with ethyl acetate(20 mL × 3). Afterwards, the combined organic layers were washed with brine (20 mL), dried over with Na2SO4, and concentrated. The crude was purified by column chromatography on silica gel to afford the desired products (3a-3i?).General procedure: To a solution of 1 (0.5 mmol) and pyridine (1.5 mL) in THF (3 mL)was added 2 (0.75 mmol) slowly at 25 C. After the complete consumption of 1 (as monitored by TLC), the reaction was quenched by the addition of 2 N HCl (5 mL) and then extracted with ethyl acetate(20 mL × 3). Afterwards, the combined organic layers were washed with brine (20 mL), dried over with Na2SO4, and concentrated. The crude was purified by column chromatography on silica gel to afford the desired products (3a-3i?).General procedure: To a solution of 1 (0.5 mmol) and pyridine (1.5 mL) in THF (3 mL)was added 2 (0.75 mmol) slowly at 25 C. After the complete consumption of 1 (as monitored by TLC), the reaction was quenched by the addition of 2 N HCl (5 mL) and then extracted with ethyl acetate(20 mL × 3). Afterwards, the combined organic layers were washed with brine (20 mL), dried over with Na2SO4, and concentrated. The crude was purified by column chromatography on silica gel to afford the desired products (3a-3i?).General procedure: To a solution of 1 (0.5 mmol) and pyridine (1.5 mL) in THF (3 mL)was added 2 (0.75 mmol) slowly at 25 C. After the complete consumption of 1 (as monitored by TLC), the reaction was quenched by the addition of 2 N HCl (5 mL) and then extracted with ethyl acetate(20 mL × 3). Afterwards, the combined organic layers were washed with brine (20 mL), dried over with Na2SO4, and concentrated. The crude was purified by column chromatography on silica gel to afford the desired products (3a-3i?).0.1 kg (0.4 mol) of 1, 4 dihydroxyindole was sequentially added to a stainless steel reaction vessel.Excess To a solution of 4-[(1-Benzyl-1H-1, 2, 3-triazol-4-yl)methoxy]-5'-ethoxy-1', 2'-dihydrospiro[cyclohexane-1, 3'-indol]-2'-one 40 (20.6'mg, 0.048'mmol) in THF (1.5'mL) at 0'C was added KOt-Bu (16.2'mg, 0.144'mmol). The reaction mixture was stirred at rt for 20'min before the addition of General procedure: Compound 5 (0.2 g, 1 mmol), Triethylamine (0.48 mL, 3.5mmol) and Arylsulfonyl chloride (1.2 mmol) into a round-bottomed flask (50 mL) were resolved inCH2Cl2. The solution was stirred at rt and stirredovernight. The reaction was quenched with water and separated to theorganic lay. Organic lay were dried over Na2SO4, and concentrated invacuum. The residue waspurified by flash silica gel columnchromatography (ethyl acetate / petroleum ether, 25%) to afford 6a-6al. The yields of the derivatives (6a-6al) were 51-83%.General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2, 4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

Molecular Weight:279.06
XLogP3:3.5
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:277.9182904
Monoisotopic Mass:277.9182904
Topological Polar Surface Area:42.5
Heavy Atom Count:15
Complexity:322
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes