Cesium carbonate → HCID 178474049, compound

To a solution of N-{4-[4-iodo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.18 mg, 0.33 mmol) in 1,4-dioxane (3 mL) was added water (0.4 mL), (2-chlorophenyl)boronic acid (0.067 g, 0.43 mmol), tetrakis (triphenylphosphine) palladium(0) (0.038 g, 0.033 mmol) and cesium carbonate (0.32 mg, 0.99 mmol). The reaction mixture was allowed to stir and was subjected to microwave irradiation at 150° C. for 20 min. The mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered and concentrated. The residue was dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). The reaction mixture was allowed to stir at rt overnight and was then concentrated. The residue was purified by column chromatography to give N-{4-[4-(2-chlorophenyl)-5-(4H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (Compound I-39) (0.095 g, 73%). LCMS (FA): m/z=395.6 (M+H).

1. customirradiation at 150° C. for 20 min
2. extractionextracted with EtOAc
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in DCM (5 mL) and to this solution
7. additionwas added TFA (2 mL)
8. stirringto stir at rt overnight
9. concentrationwas then concentrated
10. customThe residue was purified by column chromatography

ORD record

ord-6057c4d7114a43efb7cbb4678a33f2bd

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859768B2