Hydrochloric Acid → (4-Chloro-2-methyl[1,3]thiazolo[4,5-c]pyridin-7-yl)boronic acid

Temperature

-75 °C

4-Chloro-7-iodo-2-methyl-thiazolo[4,5-c]pyridine (Example B) (2.35 g, 7.56 mmol) and triisopropylborate (1.8 ml, 7.94 mmol) were dissolved in 70 ml THF and cooled to −75° C. n-Butyllithium (1.6M in hexane) (5.0 ml, 7.94 mmol) was added drop wise at −70° C. The reaction mixture was stirred for 1 hour at −75° C. and for 1 hour without ice-bath. 10 ml 2N HCl-solution were added and extracted three times with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was crystallized in acetonitrile to get the desired compound as a red solid (520 mg, 30%), MS: m/e=229.2 (M+H+).

1. additionwas added drop wise at −70° C
2. extractionextracted three times with ethyl acetate
3. washThe organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was crystallized in acetonitrile

ORD record

ord-ccdd328f3dca4370aebff2b88d4f95aa

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659401B2