Introduction of an aminomethyl group by Suzuki-Miyaura cross-coupling reaction
General Procedure for the Suzuki?Miyaura Cross-coupling Reaction: A sealed tube is charged with potassium (
tert-butoxycarbonyl)amino)methyl)trifluoroborate (62 mg, 0.263 mmol, 1.05 equiv), an aryl or heteroaryl chloride (0.25 mmol, 1.0 equiv),
Pd(OAc)2 (3 mg, 0.013 mmol, 0.05 equiv), SPhos ligand (0.03 mmol, 0.1 equiv) and K
2CO
3 (104 mg, 0.75 mmol, 3.0 equiv). The mixture is then purged with argon. Toluene/H
2O (4:1, 0.8 mL / 0.2 mL) is then added to the reaction tube. The reaction mixture is stirred for 22 h at 85 °C and then cooled to rt. A solution of pH 7 buffer (2 mL) is added, and the resulting mixture is extracted with EtOAc (2 × 3 mL). The organic layer is combined, dried (MgSO
4) and filtered. The solvent is removed in vacuo and the product is purified by column chromatography to give the corresponding compound in shown yield.