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  (Organic Chemistry)

SNAr (Br)

(Aromatic Amines)


Example 1

To a solution of the amine (A) (619 mg, 2.17 mmol) and the aryl bromide (B) (601 mg, 2.2 mmol) in IPA (15 mL) was added DIEA (0.95 mL, 5.43 mmol). The reaction mixture was stirred at reflux for 16 h, after which time was added DCM (10 mL) and sat aq NaHCO3 (15 mL). The aq layer was separated and further extracted with DCM (2 x 10 mL). The combined organics were washed with brine (10 mL), dried (Na2SO4), and concentrated. The resulting residue was purified by column chromatography (ISCO Rf, 24 g column, 100% DCM to 60:35:5 DCM/ether/MeOH) to provide the product. [1.2 g, quant]

[Patent Reference: WO2016010809, page 137, (11.8 MB)]