(2-bromophenyl)boronic acid

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:

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Chloro-2-iodo-3-[(phenylmethyl)oxy]pyridine (346 mg, 1 mmol) and 2-bromophenylboronic acid (201 mg, 1 mmol) were dissolved in 1:1 toluene/ethanol (10 ml) and potassium carbonate (1.1 g, 8 mmol) and tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmol) added. The mixture was stirred under nitrogen and heated at 90° C. for 2 hours. After cooling, diethyl ether and water were added and the organic layer washed with water, dried (MgSO4) and evaporated. The yellow oil was flash chromatographed, eluting with 2-10% ethyl acetate/isohexane to give the title compound as a clear oil (308 mg) LC/MS t=3.77, [MH+] 376, 378. added After cooling the organic layer washed with water dried (MgSO4) evaporated chromatographed eluting with 2-10% ethyl acetate/isohexane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Chloro-2-iodo-3-[(phenylmethyl)oxy]pyridine (346 mg, 1 mmol) and 2-bromophenylboronic acid (201 mg, 1 mmol) were dissolved in 1:1 toluene/ethanol (10 ml) and potassium carbonate (1.1 g, 8 mmol) and tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmol) added. The mixture was stirred under nitrogen and heated at 90° C. for 2 hours. After cooling, diethyl ether and water were added and the organic layer washed with water, dried (MgSO4) and evaporated. The yellow oil was flash chromatographed, eluting with 2-10% ethyl acetate/isohexane to give the title compound as a clear oil (308 mg) LC/MS t=3.77, [MH+] 376, 378. added After cooling the organic layer washed with water dried (MgSO4) evaporated chromatographed eluting with 2-10% ethyl acetate/isohexane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Benzyloxy)-3-bromo-5-chloropyridine (150 mg, 0.5 mmol) and 2-bromophenylboronic acid (100 mg, 0.5 mmol) were dissolved in toluene/ethanol (1:1, 5 ml) under nitrogen. Potassium carbonate (550 mg, 4 mmol) was added, followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The resulting mixture was heated at 70° C. in a Smithcreator® microwave for 10 minutes. After cooling, diethyl ether(10 ml) and water (10 ml) were added, The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane) to give the title compound as a clear oil (80 mg). After cooling The organic layer was washed with water dried (MgSO4) evaporated The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(Benzyloxy)-3-bromo-5-chloropyridine (150 mg, 0.5 mmol) and 2-bromophenylboronic acid (100 mg, 0.5 mmol) were dissolved in toluene/ethanol (1:1, 5 ml) under nitrogen. Potassium carbonate (550 mg, 4 mmol) was added, followed by tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol). The resulting mixture was heated at 70° C. in a Smithcreator® microwave for 10 minutes. After cooling, diethyl ether(10 ml) and water (10 ml) were added, The organic layer was washed with water, dried (MgSO4) and evaporated. The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane) to give the title compound as a clear oil (80 mg). After cooling The organic layer was washed with water dried (MgSO4) evaporated The product was purified by flash chromatography (silica gel, 2% ethyl acetate:isohexane)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromophenylboronic acid (1.61 g, 8.0 mmol), ethyl 5-(acetylamino)-2-bromobenzoate (2.15 g, 7.5 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (869 mg, 0.75 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (2:3) to yield 1.33 g of the title compound as a white foam. After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (2:3)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromophenylboronic acid (1.61 g, 8.0 mmol), ethyl 5-(acetylamino)-2-bromobenzoate (2.15 g, 7.5 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (869 mg, 0.75 mmol) in 1:1 toluene/ethanol (40 ml) was stirred and heated at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether and water and the organic phase dried (MgSO4) and evaporated to dryness. The residue was chromatographed with ethyl acetate/iso-hexane (2:3) to yield 1.33 g of the title compound as a white foam. After cooling the mixture the organic phase dried (MgSO4) evaporated to dryness The residue was chromatographed with ethyl acetate/iso-hexane (2:3)

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

Procedure: A mixture of 2-bromophenylboronic acid (2.01 g, 10 mmol), 4-chloro-2-iodo-1-[(phenylmethyl)oxy]benzene (3.445 g, 10 mmol), potassium carbonate (5.52 g, 40 mmol) and tetrakis(triphenylphosphine)palladium(0) (580 mg, 0.5 mmol) in 1:1 toluene/ethanol (45 ml) was stirred and heated at 90° C. under nitrogen for 2 hours when a further 1 g (4.98 mmol) of 2-bromophenylboronic acid and 0.2 g (0.17 mmol) of tetrakis(triphenylphosphine)palladium(0) were added. The mixture was heated for 6 hours then cooled, diluted with diethyl ether/water and the organic phase separated, dried (magnesium sulphate) and evaporated. The residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49) then rechromatographed eluting with dichloromethane/iso-hexane (1:9) to give 2.06 g of colourless gum which slowly crystallised. were added The mixture was heated for 6 hours then cooled the organic phase separated dried (magnesium sulphate) evaporated The residue was purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:49) then rechromatographed eluting with dichloromethane/iso-hexane (1:9)