2-METHYL-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

Conditions: temp:60.01; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:

Procedure: The general procedure A was followed using 2-methyl-1H-indole (65.6 mg, 0.5 mmol.) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 50 oC. 5y was obtained as white solid (82.3 mg, 64 %) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v). m.p.: 73-75 oC.

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

Procedure: 2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (79 mg, 185 μmol), potassium carbonate (51.1 mg, 370 μmol) and 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (95.1 mg, 370 μmol) were dissolved in dioxane (5 mL) and water (0.5 mL), then the reaction was purged with nitrogen for 1 minute. Tetrakis(triphenylphosphine)palladium(0) (21.4 mg, 18.5 μmol) was then added, and the reaction was placed under a nitrogen atmosphere and the mixture heated at to 80° C. for 2 h. Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (45 mg), was added and the reaction was heated at 80° C. for an additional 2 h. The reaction mixture was cooled, diluted with ethyl acetate/ether (ca 3:1), washed water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes) to give N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg) as an oil. MS (M+H)+=478.3. water (0.5 mL), then the reaction was purged with nitrogen for 1 minute the reaction was heated at 80° C. for an additional 2 h The reaction mixture was cooled washed water and brine dried (MgSO4) filtered concentrated in vacuo The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes)

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

Procedure: 2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (79 mg, 185 μmol), potassium carbonate (51.1 mg, 370 μmol) and 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (95.1 mg, 370 μmol) were dissolved in dioxane (5 mL) and water (0.5 mL), then the reaction was purged with nitrogen for 1 minute. Tetrakis(triphenylphosphine)palladium(0) (21.4 mg, 18.5 μmol) was then added, and the reaction was placed under a nitrogen atmosphere and the mixture heated at to 80° C. for 2 h. Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (45 mg), was added and the reaction was heated at 80° C. for an additional 2 h. The reaction mixture was cooled, diluted with ethyl acetate/ether (ca 3:1), washed water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes) to give N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg) as an oil. MS (M+H)+=478.3. water (0.5 mL), then the reaction was purged with nitrogen for 1 minute the reaction was heated at 80° C. for an additional 2 h The reaction mixture was cooled washed water and brine dried (MgSO4) filtered concentrated in vacuo The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes)

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

Procedure: 2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (79 mg, 185 μmol), potassium carbonate (51.1 mg, 370 μmol) and 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (95.1 mg, 370 μmol) were dissolved in dioxane (5 mL) and water (0.5 mL), then the reaction was purged with nitrogen for 1 minute. Tetrakis(triphenylphosphine)palladium(0) (21.4 mg, 18.5 μmol) was then added, and the reaction was placed under a nitrogen atmosphere and the mixture heated at to 80° C. for 2 h. Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (45 mg), was added and the reaction was heated at 80° C. for an additional 2 h. The reaction mixture was cooled, diluted with ethyl acetate/ether (ca 3:1), washed water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes) to give N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg) as an oil. MS (M+H)+=478.3. water (0.5 mL), then the reaction was purged with nitrogen for 1 minute the reaction was heated at 80° C. for an additional 2 h The reaction mixture was cooled washed water and brine dried (MgSO4) filtered concentrated in vacuo The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes)

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

Procedure: 2-Bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (79 mg, 185 μmol), potassium carbonate (51.1 mg, 370 μmol) and 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (95.1 mg, 370 μmol) were dissolved in dioxane (5 mL) and water (0.5 mL), then the reaction was purged with nitrogen for 1 minute. Tetrakis(triphenylphosphine)palladium(0) (21.4 mg, 18.5 μmol) was then added, and the reaction was placed under a nitrogen atmosphere and the mixture heated at to 80° C. for 2 h. Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (45 mg), was added and the reaction was heated at 80° C. for an additional 2 h. The reaction mixture was cooled, diluted with ethyl acetate/ether (ca 3:1), washed water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes) to give N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (65 mg) as an oil. MS (M+H)+=478.3. water (0.5 mL), then the reaction was purged with nitrogen for 1 minute the reaction was heated at 80° C. for an additional 2 h The reaction mixture was cooled washed water and brine dried (MgSO4) filtered concentrated in vacuo The crude residue was purified by chromatography (silica gel, 3-15% ethyl acetate in hexanes)