331950-30-2

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

Procedure: According to general procedure B, 4-bromo-N-cyclopropylbenzenesulfonamide (110 mg, 0.40 mmol), 5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid (72 mg, 0.48 mmol), potassium fluoride (76 mg, 1.3 mmol), and tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) were placed in an oven dried flask under nitrogen and dry THF (1.0 mL) was added. Tri-t-butylphosphine (60 μL, 0.02 mmol, 10 wt % in hexane) was added and the reaction was stirred for 16 hours. 4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-N-cyclopropylbenzenesulfonamide (34 mg, 28%) was provided after purification. MS (ESI) m/z 301. HPLC purity 100.0% at 210-370 nm, 9.6 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min. were placed in an oven dried flask under nitrogen dry THF (1.0 mL) was added

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

Procedure: According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and cyclopropylamine (0.27 mL, 3.90 mmol) were stirred together in dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-cyclopropylbenzenesulfonamide (0.12 g) was provided after purification. MS (ESI) m/z 276. HPLC purity 100.0% at 210-370 nm, 8.4 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

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

Procedure: According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and cyclopropylamine (0.27 mL, 3.90 mmol) were stirred together in dry dichloromethane (5 mL) for 16 hours. 4-bromo-N-cyclopropylbenzenesulfonamide (0.12 g) was provided after purification. MS (ESI) m/z 276. HPLC purity 100.0% at 210-370 nm, 8.4 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

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

Procedure: General method B was applied to 4-bromo-N-cyclopropylbenzenesulfonamide (41 mg, 0.15 mmol), 6-amino-5-(4-carbamoylphenyl)pyridin-3-ylboronic acid (53 mg, 0.15 mmol), to give 4-(2-amino-5-(4-(N-cyclopropylsulfamoyl)phenyl)pyridin-3-yl)benzamide as a white solid (29 mg, 41% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.42 (d, J=2.3 Hz, 1H), 8.03 (br. s., 1H), 7.98 (d, J=8.3 Hz, 2H), 7.90 (d, J=8.5 Hz, 2H), 7.87 (d, J=2.5 Hz, 1H), 7.80 (d, J=8.5 Hz, 2H), 7.76 (d, J=1.5 Hz, 1H), 7.61 (d, J=8.3 Hz, 2H), 7.37 (br. s., 1H), 6.06 (br. s., 2H), 2.06-2.13 (m, 1H), 0.42-0.50 (m, 2H), 0.35-0.42 (m, 2H); MS (EI) m/z: 409 [M+H]+.