methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrole-2-carboxylate synthesis
- Product Name:methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrole-2-carboxylate
- CAS Number:869886-86-2
- Molecular formula:C19H24BNO6S
- Molecular Weight:405.27
Yield:869886-86-2 86%
Reaction Conditions:
with anhydrous potassium acetate;palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride in N,N-dimethyl-formamide at 95;
Steps:
11.b
b) Title compoundTo a solution of the compound obtained in the previous section (1.00 g, 2.47 mmol) in DMF (30 ml_), bis(pinacolato)diboron (1.25 g, 4.92 mmol), potassium acetate (1.21 g, 12.34 mmol) and [1 ,1 '- bis(diphenylphosphine)ferrocene]dichloropalladium (II) (0,20 g, 0.245 mmol) were added. The reaction mixture was heated at 95 °C overnight under an Ar- atmosphere. The mixture was cooled to room temperature, the solvent was evaporated, and the residue was triturated with 200 ml_ diethyl ether. The resulting suspension was filtered and evaporated to dryness. The crude product thus obtained was chromatographed over silica gel using hexane/EtOAc mixtures of increasing polarity as eluent, to afford 0.86 g of the desired compound (86% yield). LC-MS (method 5) tR = 2.95 min; m/z = 405 (MH+).
References:
WO2008/90181,2008,A1 Location in patent:Page/Page column 68
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