2,6-dichloro-4-methylsulfonylaniline

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

Procedure: Triethylamine (1.7 mL, 12.6 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (621 mg, 4.2 mmol) and 2,6-dichloro-4-(methylsulfonyl)aniline (1 g, 4.2 mmol) in DCM (15 mL) under nitrogen. Titanium tetrachloride (1 M, 2.5 mL, 2.5 mmol) was then added and the resulting mixture was stirred for 1 hour, warmed to room temperature, and stirred for an additional 4 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid. This crude material was employed in the next step without further purification or analysis. a cooled stirred for an additional 4 hours The reaction mixture was concentrated to dryness under reduced pressure filtered though a pad of Celite® The filtrate was concentrated to dryness under reduced pressure

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

Procedure: Triethylamine (1.7 mL, 12.6 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (621 mg, 4.2 mmol) and 2,6-dichloro-4-(methylsulfonyl)aniline (1 g, 4.2 mmol) in DCM (15 mL) under nitrogen. Titanium tetrachloride (1 M, 2.5 mL, 2.5 mmol) was then added and the resulting mixture was stirred for 1 hour, warmed to room temperature, and stirred for an additional 4 hours. The reaction mixture was concentrated to dryness under reduced pressure. The residue was suspended in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid. This crude material was employed in the next step without further purification or analysis. a cooled stirred for an additional 4 hours The reaction mixture was concentrated to dryness under reduced pressure filtered though a pad of Celite® The filtrate was concentrated to dryness under reduced pressure