Potassium Phosphate, Tribasic → 3-Cyclopropyl-2-fluorobenzenamine

Temperature

100 °C

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]+.

1. customThe reaction mixture was degassed
2. temperatureThe mixture was cooled to RT
3. additiondiluted with water
4. extractionextracted twice with EtOAc
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 93-7)

ORD record

ord-54d9adda48654c5d9795e7765de66d7f

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085555B2