methyl 3-chloro-2-iodobenzoate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (1.07 g, 3 mmol, prepared as in Example 2, Step 1-2), methyl 3-chloro-2-iodobenzoate (889 mg, 3.00 mmol), Pd(OAc)2 (33.7 mg, 0.150 mmol), triphenylphosphine (79 mg, 0.300 mmol) and potassium phosphate (0.497 mL, 6.00 mmol). The vial was evacuated and backfilled with nitrogen gas 3×. Acetonitrile (8 mL) and Water (2 mL) were added and the reaction mixture was heated to 60° C. overnight in an oil bath. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (5% MeOH in DCM). Methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-chlorobenzoate was obtained as a yellow powder. The vial was evacuated Acetonitrile (8 mL) and Water (2 mL) were added The reaction mixture was partitioned between water and ethyl acetate The organic phase was separated dried over MgSO4 The solvent was removed under reduced pressure the residue was purified by column chromatography (5% MeOH in DCM)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vial was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (1.07 g, 3 mmol, prepared as in Example 2, Step 1-2), methyl 3-chloro-2-iodobenzoate (889 mg, 3.00 mmol), Pd(OAc)2 (33.7 mg, 0.150 mmol), triphenylphosphine (79 mg, 0.300 mmol) and potassium phosphate (0.497 mL, 6.00 mmol). The vial was evacuated and backfilled with nitrogen gas 3×. Acetonitrile (8 mL) and Water (2 mL) were added and the reaction mixture was heated to 60° C. overnight in an oil bath. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (5% MeOH in DCM). Methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-chlorobenzoate was obtained as a yellow powder. The vial was evacuated Acetonitrile (8 mL) and Water (2 mL) were added The reaction mixture was partitioned between water and ethyl acetate The organic phase was separated dried over MgSO4 The solvent was removed under reduced pressure the residue was purified by column chromatography (5% MeOH in DCM)