2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline synthesis
- Product Name:2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
- CAS Number:876922-75-7
- Molecular formula:C16H20BNO2
- Molecular Weight:269.15
698981-68-9
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Yield:876922-75-7 81%
Reaction Conditions:
with potassium acetate;1,1'-bis-(diphenylphosphino)ferrocene;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 80;
Steps:
160
Description 160; 2-Methvl-5-(4.4.5.5-tetramethvl-1 .3.2-dioxaborolan-2-vl)quinoline (D160); A mixture of 2-methyl-5-quinolinyl trifluoromethanesulfonate (preparation reported inWO 2004046124 A1) (13.5g 0.046 mol), bis(pinacolato)diboron (13 g, 0.051 mol),[1,1'-bis(diphenylphosphino)ferrocene] dichloro palladium complex (1.88 g, 0.0023mol), 1,1'-bis(diphenylphosphino)ferrocene (1.27g, 0.0023 mol) and potassiumacetate (13.5g, 0.138 mol) in dry 1,4 dioxane (120 ml) was heated overnight at 80°C.Solvent was evaporated to dryness and the crude material purified on a Horizoncolumn (65M) eluting with 10% ethyl acetate in cyclohexane to afford the titlecompound as a cream solid (10g, 81%);
References:
WO2006/24517,2006,A1 Location in patent:Page/Page column 105