4-Chlorophenyl trifluoromethanesulfonate

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

Procedure: Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.28 mmol) was reacted with 4-chlorophenyl trifluoromethanesulfonate (74 mg, 0.28 mmol) to afford the desired 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.69–8.68 (d, 1H), 7.98 (s, 2H), 7.94–7.90 (m, 2H), 7.86–7.78 (m, 1H), 7.74–7.73 (m, 1H), 7.65–7.58 (m, 1H), 7.40–7.37 (m, 2H), 4.03 (s, 3H). MS (ESI) 337 (M+H)+.

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

Procedure: Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.28 mmol) was reacted with 4-chlorophenyl trifluoromethanesulfonate (74 mg, 0.28 mmol) to afford the desired 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.69–8.68 (d, 1H), 7.98 (s, 2H), 7.94–7.90 (m, 2H), 7.86–7.78 (m, 1H), 7.74–7.73 (m, 1H), 7.65–7.58 (m, 1H), 7.40–7.37 (m, 2H), 4.03 (s, 3H). MS (ESI) 337 (M+H)+.

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

Procedure: Utilizing the general procedure outlined in the synthesis of 2-[4-(6-bromopyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole, 2-[3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole (100 mg, 0.28 mmol) was reacted with 4-chlorophenyl trifluoromethanesulfonate (74 mg, 0.28 mmol) to afford the desired 2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.69–8.68 (d, 1H), 7.98 (s, 2H), 7.94–7.90 (m, 2H), 7.86–7.78 (m, 1H), 7.74–7.73 (m, 1H), 7.65–7.58 (m, 1H), 7.40–7.37 (m, 2H), 4.03 (s, 3H). MS (ESI) 337 (M+H)+.