2-fluorobenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in step 2 of Example 18 from 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate and 2-fluorobenzenesulfonamide. MS (ESI) n/z 500 [M+H]+, 498 [M−H]−, 1H-NMR (CDCl3) δ 1.23 (3H, t, J=6.0 Hz), 2.71 (2H, q, J=6.0 Hz), 2.84 (2H, t, J=6.0 Hz), 3.44-3.52 (2H, m), 6.58 (1H, br), 7.18-7.30 (7H, m), 7.37 (2H, t, J=9.0 Hz), 7.59-7.65 (1H, m), 7.78 (2H, d, J=6.0 Hz), 7.84-7.90 (2H, m).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in step 2 of Example 18 from 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate and 2-fluorobenzenesulfonamide. MS (ESI) n/z 500 [M+H]+, 498 [M−H]−, 1H-NMR (CDCl3) δ 1.23 (3H, t, J=6.0 Hz), 2.71 (2H, q, J=6.0 Hz), 2.84 (2H, t, J=6.0 Hz), 3.44-3.52 (2H, m), 6.58 (1H, br), 7.18-7.30 (7H, m), 7.37 (2H, t, J=9.0 Hz), 7.59-7.65 (1H, m), 7.78 (2H, d, J=6.0 Hz), 7.84-7.90 (2H, m).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.6 of 2-methoxyethyl-mercaptan is added dropwise to a mixture of 3.5 g of 55% sodium hydride and 80 ml of dimethylformamide. To this mixture 8.0 of 2-fluorophenylsulfonamide are added. The reaction mixture is stirred for 3 hours at a temperatur of 115°-120° C. After cooling the mixture is poured into water. To this mixture 10% of hydrochlorid acid are added, and the product is extracted with ethyl acetate. The organic phase is evaporated and the residue is purified by chromatography. Yield: 6.7 g of 2-methoxyethylthio-phenylsulfonamide, m.p. 119°-121° C. After cooling the mixture the product is extracted with ethyl acetate The organic phase is evaporated the residue is purified by chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in step 1 of Example 42 from phenyl 2-{4-[5-methyl-4-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethylcarbamate (step 7 of Example 52) and 2-fluoro-benzenesulfonamide: MS (ESI) m/z 547 [M+H]+, 545 [M−H]−, 1H-NMR (CDCl3) δ 7.86-7.81 (1H, m), 7.74-7.58 (1H, m), 7.48-7.24 (1H, m), 6.45 (1H, br.s) 3.54-3.49 (2H, m), 2.87 (2H, t, J=6.7 Hz), 2.23 (3H, s).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in step 1 of Example 42 from phenyl 2-{4-[5-methyl-4-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethylcarbamate (step 7 of Example 52) and 2-fluoro-benzenesulfonamide: MS (ESI) m/z 547 [M+H]+, 545 [M−H]−, 1H-NMR (CDCl3) δ 7.86-7.81 (1H, m), 7.74-7.58 (1H, m), 7.48-7.24 (1H, m), 6.45 (1H, br.s) 3.54-3.49 (2H, m), 2.87 (2H, t, J=6.7 Hz), 2.23 (3H, s).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared according to the procedure described in step 2 of Example 22 from phenyl 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylcarbamate (step 1 of Example 22) and 2-fluorobenzenesulfonamide: 1H-NMR (CDCl3) δ 7.89 (1H, t, J=6.9 Hz), 7.45-7.06 (12H, m), 6.48 (1H, br.s), 3.46-3.36 (2H, m),2.77-2.71 (2H, m), 2.28 (3H, s), 2.21 (3H, s).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl alcohol (1 g, 8.6 mmol) in 10 mL of dry DMF was added to NaH (0.7 g, 17.1 mmol.) at 0° C. The reaction mixture was stirred at 0° C. for 30 min under N2. To the resulting mixture was added 2-sulfamoyl fluorobenzene (1 g, 5.7 mmol.) in 20 mL of dry DMF. The reaction mixture was stirred at 80-90° C. for 3 hours. After cooling to r.t., the reaction mixture was poured into ice-water and neutralized with aq. HCl (2 M) to pH 7. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was over Na2SO4, filtered and concentrated to afford crude 1-(phenoxymethyl)-2-sulfamoylbenzene (1 g, 66.7%), which was used directly without further purification. The reaction mixture was stirred at 80-90° C. for 3 hours After cooling to r.t. The mixture was extracted with ethyl acetate (3×50 mL) filtered concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of benzyl alcohol (1 g, 8.6 mmol) in 10 mL of dry DMF was added to NaH (0.7 g, 17.1 mmol.) at 0° C. The reaction mixture was stirred at 0° C. for 30 min under N2. To the resulting mixture was added 2-sulfamoyl fluorobenzene (1 g, 5.7 mmol.) in 20 mL of dry DMF. The reaction mixture was stirred at 80-90° C. for 3 hours. After cooling to r.t., the reaction mixture was poured into ice-water and neutralized with aq. HCl (2 M) to pH 7. The mixture was extracted with ethyl acetate (3×50 mL). The combined organic layer was over Na2SO4, filtered and concentrated to afford crude 1-(phenoxymethyl)-2-sulfamoylbenzene (1 g, 66.7%), which was used directly without further purification. The reaction mixture was stirred at 80-90° C. for 3 hours After cooling to r.t. The mixture was extracted with ethyl acetate (3×50 mL) filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Fluorobenzenesulfonamide was reacted with 4-bromothiophenol according to the method of Example 46 Step 1 using 1-methyl-2-pyrrolidinone as solvent. The resulting thioether was oxidised to the corresponding sulfoxide by the procedure of Example 16 Step 1. This was coupled with 4-fluorostyrene by the procedure of Example 107 to give the title compound. δH (500 MHz, d6 DMSO): 8.10 (1H, d, J=7.8 Hz), 7.91 (1H, d, J=7.7 Hz), 7.87 (2H, s), 7.81 (1H, t, J=7.4 Hz), 7.71-7.63 (7H, m), 7.31 (1H, d, J=16.5 Hz), 7.22-7.18 (3H, m).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Fluorobenzenesulfonamide was reacted with 4-bromothiophenol according to the method of Example 46 Step 1 using 1-methyl-2-pyrrolidinone as solvent. The resulting thioether was oxidised to the corresponding sulfoxide by the procedure of Example 16 Step 1. This was coupled with 4-fluorostyrene by the procedure of Example 107 to give the title compound. δH (500 MHz, d6 DMSO): 8.10 (1H, d, J=7.8 Hz), 7.91 (1H, d, J=7.7 Hz), 7.87 (2H, s), 7.81 (1H, t, J=7.4 Hz), 7.71-7.63 (7H, m), 7.31 (1H, d, J=16.5 Hz), 7.22-7.18 (3H, m).