[2-(dimethylsulfamoyl)phenyl]boronic acid

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

Procedure: 5-Iodo-2-aminobenzenesulfonamide (see compound 37) was transformed by Method H (using 2-(N,N-dimethylsulfamoyl)phenylboronic acid) and Method G (using cyclohexanecarboxaldehyde). M.p. 290-300° C.

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane

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

Procedure: 5-Iodo-2-aminobenzenesulfonamide (see compound 37) was transformed by Method H (using 2-(N,N-dimethylsulfamoyl)phenylboronic acid) and Method G (using cyclohexanecarboxaldehyde). M.p. 290–300° C.

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane

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

Procedure: The title compound was prepared in a manner similar to that described in Example 589 using 5-(4-bromo-2-methylphenyl)pyrazin-2-amine and (2-(N,N-dimethylsulfamoyl)phenyl)boronic acid. MS (ESI): mass calcd. for C19H20N4O2S, 368.46; m/z found, 369.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=1.5, 1H), 8.12 (dd, J=8.0, 1.3, 1H), 8.10 (d, J=1.5, 1H), 7.60-7.55 (m, 1H), 7.52-7.47 (m, 1H), 7.43 (d, J=7.8, 1H), 7.35-7.29 (m, 3H), 4.77 (s, 2H), 2.44 (s, 3H), 2.42 (s, 6H).

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 20 mL vial were 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine (50 mg, 0.19 mmol), (2-(N,N-dimethylsulfamoyl)phenyl)boronic acid, K2CO3 (43 mg, 0.19 mmol), and Pd(dppf)Cl2.CH2Cl2 (8 mg, 0.009 mmol), and a stir-bar. The vial was sealed with a teflon lined cap and sparged with N2. The vial was then charged with freshly sparged DMSO (2 mL) and then stirred 16 hours at 80° Celsius. The reaction mixture was then cooled to rt, filtered, and purified by HPLC to give the title compound (36 mg, 40%). MS (ESI): mass calcd. for C18H17FN4O2S, 372.11; m/z found, 373.2 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.33 (s, 2H), 8.06-7.96 (m, 2H), 7.72-7.67 (m, 1H), 7.64-7.59 (m, 1H), 7.43-7.39 (m, 1H), 7.32-7.26 (m, 2H), 2.49 (s, 6H). lined cap sparged with N2 The vial was then charged with freshly sparged DMSO (2 mL) The reaction mixture was then cooled to rt filtered purified by HPLC

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

Procedure: 5-Iodo-2-aminobenzenesulfonamide (see compound 37) was transformed by Method H (using 2-(N,N-dimethylsulfamoyl)phenylboronic acid) and Method G (using cyclohexanecarboxaldehyde). M.p. 290-300° C.

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N,N-dimethylbenzenesulfonamide (9.25 g; 50 mmol) in dry Et2O (150 ml) under N2 was cooled to −70° C. and added a solution of 2.5 M n-BuLi in hexane (24 ml; 60 mmol) such that the reaction temperature was kept below −60° C. The cooling bath was removed and the reaction mixture allowed to slowly warm up to +20° C. The reaction mixture was re-cooled to −70° C. and B(Oi-Pr)3 (16.1 ml; 70 mmol) was added. The reaction mixture was left cold and allowed to warm up over night, 1 M HCl (100 ml) was added and stirring was continued at rt. for 1 h. The reaction mixture was then extracted with Et2O (2×50 ml) and the combined organic fractions extracted with 1 M NaOH (4×50 ml). The combined aqueous fractions were neutralized with 1 M HCl and extracted with Et2O (4×100 ml). The combined organic fractions were dried (Na2SO4) and evaporated to dryness, washed with Et2O/hexane to give 3.4 g (30%) product. was kept below −60° C The cooling bath was removed to slowly warm up to +20° C The reaction mixture was left cold to warm up over night was continued at rt The reaction mixture was then extracted with Et2O (2×50 ml) the combined organic fractions extracted with 1 M NaOH (4×50 ml) extracted with Et2O (4×100 ml) The combined organic fractions were dried (Na2SO4) evaporated to dryness washed with Et2O/hexane