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1H-Benzotriazole, 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- synthesis
- Product Name:1H-Benzotriazole, 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
- CAS Number:1396753-41-5
- Molecular formula:C13H18BN3O2
- Molecular Weight:259.11
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Yield:1396753-41-5 74%
Reaction Conditions:
with anhydrous potassium acetate;palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride in 1,4-dioxane at 90; for 12 h;Inert atmosphere;
Steps:
95.4
Methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-7H-benzo[i/][l,2,3]triazoleTo a solution of 5-bromo-l-methyl-iH-benzo[2 (86 mg, 0.12 mmol), AcOK (0.575 g, 5.86 mmol), and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (658 mg, 2.59 mmol) under an N2 atmosphere. The resulting solution was stirred for 12 h at 90°C and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (2% ethyl acetate in petroleum ether) to afford l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-7H-benzo[i/][l,2,3]triazole as a white solid (0.56 g, 74%).LC/MS (ES, m/z): [M+H]+.260.1*H-NMR (300 MHz, CDCI3) δ 8.57 (s, 1H), 7.90 - 7.93 (m, 1H), 7.50 - 7.55 (m, 1H), 4.33 (s, 3H), 1.36 (s, 12H)
References:
WO2012/119046,2012,A2 Location in patent:Page/Page column 208
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