2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → N,N-Dimethyl-3-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxy)propan-1-amine

온도

18 °C

Butyllithium (2.5N, 4.8 mL, 50.96 mmol) was added to a solution of 3-(5-bromopyridin-2-yl)oxy-N,N-dimethylpropan-1-amine (2.07 g, 7.99 mmol) and 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (2.79 g, 15.00 mmol) in THF (20 mL) at −78° C. over 10 minutes under an inert atmosphere. The resulting solution was stirred for 4 h at 18° C. The reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride then partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was concentrated in vacuo and the residue purified by FCC, eluting with EtOAc/petroleum ether (1:3) to afford the desired material (270 mg, 11%) as a yellow solid. Mass Spectrum: m/z (ES+)[M+H]+=225.

1. customThe reaction was then quenched by the addition of a sat. aqueous solution of ammonium chloride
2. customthen partitioned between EtOAc (100 mL) and water (100 mL)
3. concentrationThe organic layer was concentrated in vacuo
4. customthe residue purified by FCC
5. washeluting with EtOAc/petroleum ether (1:3)

ORD 기록

ord-3e069e9040904f1999813d7bf5c39f01

출처 데이터셋

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09428503B2