3-cyclopropyl-2-fluoroaniline

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-bromo-2-fluoroaniline (200 mg, 1.05 mmol), cyclopropylboronic acid (118 mg, 1.37 mmol), potassium phosphate (782 mg, 3.68 mmol), and tricyclohexylphosphine (29.5 mg, 0.105 mmol) in toluene (2.4 mL) and water (120 μL) was added Pd(OAc)2 (11.8 mg, 0.05 mmol). The reaction mixture was degassed by repeating alternating application of vacuum and positive nitrogen pressure (3×), and then heated at 100° C. under nitrogen overnight. The mixture was cooled to RT, diluted with water, and extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 93-7). TLC, Rf hexane/EtOAc 2:1)=0.7; MS (UPLC/MS): 152.0 [M+H]+. The reaction mixture was degassed The mixture was cooled to RT diluted with water extracted twice with EtOAc The combined organic layers were dried (Na2SO4) filtered concentrated The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 93-7)