N,N,2-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide synthesis

Yield:1011731-99-9 73%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane;Reflux;Inert atmosphere;

Steps:

A.43-2 Step 43-2: N,N,2-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

4-bromo-N, N, 2-trimethylbenzamide (28.0 g, 115 mmol) , BPD (44.0 g, 174 mmol) , Pd (dppf) Cl₂(5.1 g, 6.94 mmol) and AcOK (22.7 g, 231 mmol) was added to dioxane (400 mL) under nitrogen. The reaction mixture was heated to reflux overnight then cooled to room temperature. EtOAc (400 mL) was added and the mixture was washed with brine (300 mL x 2) . The aqueous layer was extracted with EtOAc (400 mL) . The combined organic layer was dried over Na₂SO₄then concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with EtOAc/PE (15%to 70%) to give the title compound (26.0 g, 73%) . LC-MS (M+H)⁺=290.1.

References:

WO2020/103896,2020,A1 Location in patent:Page/Page column 67