1-[(3-bromophenyl)methyl]-4-methylpiperazine

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

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

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

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

Procedure: 98 mg 4-Carboxybenzeneboronic acid, 159 mg 1-(3-Bromo-benzyl)-4-methyl-piperazine, 410 mg potassium carbonate, and 69 mg tetrakis-triphenylphosphino-palladium were stirred under an argon atmosphere in a mixture of 1 ml dioxane and 1 ml water at 85 C for 16 hrs. The mixture was cooled to RT, diluted with 100 ml water and filtered. The filtrate was carefully treated with conc. HCl until the product precipitated. Filtration and drying of the residue yielded 190 mg of the title product. filtered The filtrate was carefully treated with conc. HCl until the product precipitated Filtration drying of the residue

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

Procedure: 0.30 g 1-Methylpiperazine in 2 ml THF were treated dropwise at RT with a solution of 0.5 g 3-bromobenzyl bromide in 3 ml THF. After stirring for 2 hrs, the mixture was heated to 60 C for 30 min. The solvent was evaporated and the residue chromatographed on silica using a gradient from heptane to heptane/dichloromethane/conc. ammonia (4/6/0.5). the mixture was heated to 60 C for 30 min The solvent was evaporated the residue chromatographed on silica using a gradient from heptane to heptane/dichloromethane/conc

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

Procedure: [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.043, 35%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.27 (d, J=8.6 Hz, 2H), 8.13 (d, J=8.6 Hz, 2H), 7.59-7.51 (m, 3H), 7.45-7.43 (m, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.06 (dd, J=5.1, 3.3 Hz, 1H), 6.98-6.94 (m, 2H), 3.50 (s, 2H), 3.15 (s, 3H), 2.70-2.32 (m, 8H), 2.28 (s, 3H). MS=477 (MH)+. Product isolated as a yellow foam (0.043, 35%)

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

Procedure: [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.043, 35%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.27 (d, J=8.6 Hz, 2H), 8.13 (d, J=8.6 Hz, 2H), 7.59-7.51 (m, 3H), 7.45-7.43 (m, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.06 (dd, J=5.1, 3.3 Hz, 1H), 6.98-6.94 (m, 2H), 3.50 (s, 2H), 3.15 (s, 3H), 2.70-2.32 (m, 8H), 2.28 (s, 3H). MS=477 (MH)+. Product isolated as a yellow foam (0.043, 35%)

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

Procedure: [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (29.0 mg, 0.0530 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.036 g, 29%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.6 Hz, 1H), 8.24 (d, J=8.5 Hz, 2H), 8.09 (d, J=8.5 Hz, 2H), 7.66 (dd, J=7.4, 0.9 Hz, 1H), 7.58 (dd, J=7.8, 1.9 Hz, 1H), 7.46 (s, 1H), 7.31 (t, J=7.8 Hz, 1H), 7.02 (t, J=7.2 Hz, 1H), 6.98 (d, J=7.5 Hz, 1H), 6.90 (s, 1H), 3.54 (s, 2H), 3.10 (s, 3H), 2.70-2.32 (m, 8H), 2.29 (s, 3H). MS=477 (MH)+.

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

Procedure: [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (29.0 mg, 0.0530 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.036 g, 29%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.6 Hz, 1H), 8.24 (d, J=8.5 Hz, 2H), 8.09 (d, J=8.5 Hz, 2H), 7.66 (dd, J=7.4, 0.9 Hz, 1H), 7.58 (dd, J=7.8, 1.9 Hz, 1H), 7.46 (s, 1H), 7.31 (t, J=7.8 Hz, 1H), 7.02 (t, J=7.2 Hz, 1H), 6.98 (d, J=7.5 Hz, 1H), 6.90 (s, 1H), 3.54 (s, 2H), 3.10 (s, 3H), 2.70-2.32 (m, 8H), 2.29 (s, 3H). MS=477 (MH)+.

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

Procedure: [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.043, 35%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.27 (d, J=8.6 Hz, 2H), 8.13 (d, J=8.6 Hz, 2H), 7.59-7.51 (m, 3H), 7.45-7.43 (m, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.06 (dd, J=5.1, 3.3 Hz, 1H), 6.98-6.94 (m, 2H), 3.50 (s, 2H), 3.15 (s, 3H), 2.70-2.32 (m, 8H), 2.28 (s, 3H). MS=477 (MH)+. Product isolated as a yellow foam (0.043, 35%)

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

Procedure: [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-ylmethyl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 1-(3-bromo-benzyl)-4-methyl-piperazine (77.0 mg, 0.286 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (29.0 mg, 0.0530 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.036 g, 29%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.6 Hz, 1H), 8.24 (d, J=8.5 Hz, 2H), 8.09 (d, J=8.5 Hz, 2H), 7.66 (dd, J=7.4, 0.9 Hz, 1H), 7.58 (dd, J=7.8, 1.9 Hz, 1H), 7.46 (s, 1H), 7.31 (t, J=7.8 Hz, 1H), 7.02 (t, J=7.2 Hz, 1H), 6.98 (d, J=7.5 Hz, 1H), 6.90 (s, 1H), 3.54 (s, 2H), 3.10 (s, 3H), 2.70-2.32 (m, 8H), 2.29 (s, 3H). MS=477 (MH)+.

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

Procedure: 0.30 g 1-Methylpiperazine in 2 ml THF were treated dropwise at RT with a solution of 0.5 g 3-bromobenzyl bromide in 3 ml THF. After stirring for 2 hrs, the mixture was heated to 60 C for 30 min. The solvent was evaporated and the residue chromatographed on silica using a gradient from heptane to heptane/dichloromethane/concentrated ammonia (4/6/0.5). the mixture was heated to 60 C for 30 min The solvent was evaporated the residue chromatographed on silica using a gradient from heptane to heptane/dichloromethane/concentrated ammonia (4/6/0.5)