3-Tert-butyl-2-methoxy-5-(2-methoxy-3-pyridyl)benzaldehyde → (3-Amino-phenyl)-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-methanol

Participants

Reaction Steps

step 1—To a solution of 3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-benzaldehyde (B-2a, R4=tert-Bu, R6═H, 110 mg, 0.368 mmol) in THF (5 mL) at 0° C. was added a solution of 3-(bis-(trimethylsilyl)amino)phenyl magnesium chloride (1.0 M in THF, 0.750 mL, 0.750 mmol). The reaction was gradually warmed RT and stirred overnight. The reaction mixture was quenched with 1N aqueous HCl solution and extracted with EtOAc. The organic layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25 to 50% EtOAc) to afford 79 mg (55%) of (3-amino-phenyl)-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-methanol (34) as a colorless oil.

Provenance & Evidence