Yield:741709-62-6 1.2g

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 100; for 2 h;

Steps:

188.a Example 188 (S)-4-(4-(3-(1-Cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl)pyrimidin-2-yl)picolinonitrile
Step a. To a solution of 4-chloro-2-pyridinecarbonitrile (0.700 g, 5.05 mmol) in 1,4-dioxane (14 ml) were added dis(pinacolato)diboron (1.920 g, 7.57 mmol) and potassium acetate (1.53 g, 15.7 mmol) at rt. The reaction mixture was degassed for 15 min before addition of Pd(dppf)C_1-2 (0.184 g, 0.252 mmol). The reaction was heated at 100° C. for 2 h. The resulting reaction mixture was cooled to rt, combined with one other batch prepared on the same scale by an identical method, diluted with water (40 ml) and extracted with EtOAc (2×40 ml). The combined organic layer was dried over Na₂SO₄, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (5% EtOAc in hexane) yielding 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile (1.200 g, 5.22 mmol). LCMS: Method C, 1.136, MS: ES+149.20 [M-81]

References:

MISSION THERAPEUTICS LIMITED;JONES, Alison;KEMP, Mark Ian;STOCKLEY, Martin Lee;WOODROW, Michael D. US2020/331888, 2020, A1 Location in patent:Paragraph 1006-1007