3-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzaMide synthesis

Yield:631911-09-6 71%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 100; for 3 h;Sealed tube;Inert atmosphere;

Steps:

47.1 Step 1:
3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide


To a sealed tube was added 4-bromo-3-methyl-benzamide (1.0 g, 4.67 mmol), bis(pinacolato)diboron (1.4 g, 5.61 mol), potassium acetate (1.4 g, 14.01 mmol), Pd(dppf)Cl₂ (341 mg, 0.47 mmol) and 1,4-dioxane (10 mL).
The mixture was bubbled through with N₂ for 2 minutes and stirred at 100° C. for 3 hours.
The mixture was concentrated in vacuo and purified by silica gel chromatography (petroleum ether/ethyl acetate, 1:1 to 0:100) to afford 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (920 mg, 71% yield) as a white solid. LCMS (ESI) [M+H]⁺=262.2.

References:

US2018/282328,2018,A1 Location in patent:Paragraph 0923; 0924