N-Phenyl diethanolamine → 2-Methyl-2-(6-(6-phenyl-1,3,6,2-dioxazaborocan-2-yl)pyridin-2-yl)propanenitrile

A stirred solution of 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (1 g, 4.44 mmol) and triisopropylborate (1.23 ml, 5.33 mmol) in tetrahydrofuran (10 ml) was cooled down to −75° C. A 2.5 M solution of n-BuLi in hexanes (2.31 ml, 5.77 mmol) was added at such a rate that the temperature did not exceed −67° C. After complete addition, the reaction was allowed to warm to room temperature and was stirred at this temperature for 16 hours. After this time, a solution of N-phenyldiethanolamine (805 mg, 4.44 mmol) in THF (8 ml) was added and the resulting mixture was heated at reflux for 4 hours. The mixture was concentrated in vacuo, diluted with isopropanol (18 ml) and refluxed for 1 hour. The reaction mixture was cooled down to room temperature and stirred for 18 hours. The newly formed solid was filtered off and dried under vacuo at 40° C. to afford the title compound as a white solid (880 mg, 59% yield).

1. customdid not exceed −67° C
2. additionAfter complete addition
3. temperaturethe resulting mixture was heated
4. temperatureat reflux for 4 hours
5. concentrationThe mixture was concentrated in vacuo
6. additiondiluted with isopropanol (18 ml)
7. temperaturerefluxed for 1 hour
8. temperatureThe reaction mixture was cooled down to room temperature
9. stirringstirred for 18 hours
10. filtrationThe newly formed solid was filtered off
11. customdried under vacuo at 40° C.

ORD record

ord-14e64df879de475e9c112e6ab4fd34be

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367697B2