(4-bromophenyl)cyanamide

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

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-ethylaniline (20.6 g, 103 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The amine hydrobromide was filtered off, and the filtrate was concentrated in vacuo at room temperature and triturated with hexane to give 4-bromophenylcyanamide (2.3 g, 10%) as an off white solid. HRMS: calcd for C9H9BrN2+H+, 225.00218; found (ESI-FTMS, [M+H]+), 225.00277. The amine hydrobromide was filtered off the filtrate was concentrated in vacuo at room temperature triturated with hexane

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-methylaniline (Aldrich Chemical Company) (19.15 g, 103.4 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The reaction was filtered, and the filtrate was concentrated in vacuo at room temperature to give 4-bromophenylcyanamide (8.5 g, 92%) as an off white solid. HRMS: calcd for C8H7BrN2, 209.97926; found (EI, M+), 209.9788. The reaction was filtered the filtrate was concentrated in vacuo at room temperature

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

Procedure: 4-bromophenylcyanamide (0.651 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium (76 mg, 0.078 mmol), N-methyl-5-cyanopyrroleboronic acid (1.1 g, 7.3 mmol), and potassium fluoride (0.776 g, 13.2 mmol) were placed in a 40 mL vial fitted with a septa. The vial was then filled with a continuous flow of nitrogen and THF (10 mL) was added. tri-Tert-butylphosphine (10 wt % in hexane) (0.486 mL, 0.078 mmol) was added to the mixture and allowed to stir 3 hours at 50° C. until the starting bromide was consumed. The mixture was then diluted with 1/1 hexane/ethylacetate, filtered through a plug of silica gel, the solvent was evaporated and the residue was flash chromatographed using 5/1, 4/1, then 3/2 Hexane/Ethylacetate to give (0.250 g, 33%) of the title compound. vial fitted with a septa was added was consumed The mixture was then diluted with 1/1 hexane/ethylacetate filtered through a plug of silica gel the solvent was evaporated chromatographed

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol), and 4-bromoaniline (17.8 g, 103.4 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The reaction was filtered, and the filtrate was concentrated in vacuo at room temperature to give 4-bromophenylcyanamide (8.5 g, 92%) as an off white solid. The reaction was filtered the filtrate was concentrated in vacuo at room temperature

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-ethylaniline (20.6 g, 103 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The amine hydrobromide was filtered off, and the filtrate was concentrated in vacuo at room temperature and triturated with hexane to give 4-bromophenylcyanamide (2.3 g, 10%) as an off white solid. HRMS: calcd for C9H9BrN2+H+, 225.00218; found (ESI-FTMS, [M+H]+), 225.00277. The amine hydrobromide was filtered off the filtrate was concentrated in vacuo at room temperature triturated with hexane

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol) and 4-bromo-2-methylaniline (Aldrich Chemical Company) (19.15 g, 103.4 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The reaction was filtered, and the filtrate was concentrated in vacuo at room temperature to give 4-bromophenylcyanamide (8.5 g, 92%) as an off white solid. HRMS: calcd for C8H7BrN2, 209.97926; found (EI, M+), 209.9788. The reaction was filtered the filtrate was concentrated in vacuo at room temperature

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

Procedure: 4-bromophenylcyanamide (0.651 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium (76 mg, 0.078 mmol), N-methyl-5-cyanopyrroleboronic acid (1.1 g, 7.3 mmol), and potassium fluoride (0.776 g, 13.2 mmol) were placed in a 40 mL vial fitted with a septa. The vial was then filled with a continuous flow of nitrogen and THF (10 mL) was added. tri-Tert-butylphosphine (10 wt % in hexane) (0.486 mL, 0.078 mmol) was added to the mixture and allowed to stir 3 hours at 50° C. until the starting bromide was consumed. The mixture was then diluted with 1/1 hexane/ethylacetate, filtered through a plug of silica gel, the solvent was evaporated and the residue was flash chromatographed using 5/1, 4/1, then 3/2 Hexane/Ethylacetate to give (0.250 g, 33%) of the title compound. vial fitted with a septa was added was consumed The mixture was then diluted with 1/1 hexane/ethylacetate filtered through a plug of silica gel the solvent was evaporated chromatographed

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

Procedure: A mixture of cyanogen bromide (5.0 g, 47 mmol), and 4-bromoaniline (17.8 g, 103.4 mmol) in diethylether (150 mL) was stirred for 3 days under nitrogen atmosphere. The reaction was filtered, and the filtrate was concentrated in vacuo at room temperature to give 4-bromophenylcyanamide (8.5 g, 92%) as an off white solid. The reaction was filtered the filtrate was concentrated in vacuo at room temperature