N,N,N',N'-Tetramethylethylenediamine → (2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

Temperature

-70 °C

A solution of tetrahydrofuran (400 mL) of pyridin-2-yl-carbamic acid tert-butyl ester (16 g) described in Manufacturing Example 1-7-1 and N,N,N′,N′-tetramethylethylene diamine (25 g) was cooled to −70° C., n-butyl lithium (78 mL, 2.64 M heptane solution) was added dropwise for 1 hour, and the mixture was stirred for 10 minutes. This mixture was then warmed to between −10° C. and −6° C., and stirred at that temperature for 2 hours. The solution was then cooled again to −70° C., and triisobutyl borate (58 g) was added dropwise for 1 hour. The mixture was warmed to 0° C., and saturated aqueous ammonium chloride solution was added thereto. To the resulting yellow solids was added ether and then stirred, and the solids were filtered and washed with ether and water. The solids were dried under a reduced pressure to obtain the title compound (14 g).

1. temperatureThis mixture was then warmed to between −10° C. and −6° C.
2. stirringstirred at that temperature for 2 hours
3. temperatureThe solution was then cooled again to −70° C.
4. temperatureThe mixture was warmed to 0° C.
5. stirringstirred
6. filtrationthe solids were filtered
7. washwashed with ether and water
8. customThe solids were dried under a reduced pressure

ORD record

ord-0bdc8ad9c7b54110a1c9860c9ef7b31f

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188119B2