1H-Pyrrolo[2,3-c]pyridin-5-amine(9CI)

General procedure: To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below.General procedure: To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below.General procedure: To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below.To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below. 4.1.3.1 3, 4-Dichloro-N-(1H-pyrrolo[2, 3-c]pyridin-5-yl)benzamide (10) (0045) The compound was prepared using of Intermediate 5 (200 mg, 0.450 mmol) , 1H-pyrrolo [2, 3-c] pyridin-5-amine (120 mg, 0.90 mmol) , palladium (II) acetate (50 mg, 0.225 mmol) , xantphos (196 mg, 0.340 mmol) and potassium carbonate (124 mg, 0.90 mmol) in 1, 4-dioxane (10 mL) under heating at 100 through microwave irradiation for 1 hour under N2 atmosphere. LC-MS: m/z 539.2 (M+H) +.e 5-(1, 2, 4-Triazol-4-yl)-1H-pyrrolo[2, 3-c]pyridine