1-(3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol synthesis

2synthesis methods

Product Name:1-(3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol
CAS Number:1082503-78-3
Molecular formula:C15H27BN2O3
Molecular Weight:294.1975

558-30-5 Synthesis

558-30-5
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3,5-DIMETHYLPYRAZOLE-4-BORONIC ACID, PINACOL ESTER

857530-80-4
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$9.00/250mg

1-(3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol

1082503-78-3
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Yield:-

Reaction Conditions:

Stage #1:3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole with sodium hydride in N,N-dimethyl-formamide for 0.166667 h;
Stage #2:2-methyl-1,2-epoxypropane in N,N-dimethyl-formamide at 80;

Steps:

5
1-[3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-2-methylpropan-2-ol A solution of 3,5-dimethylpyrazole-4-boronic acid, pinacol ester (200.0 mg, 0.9005 mmol) in DMF (4 mL, 50 mmol) was added sodium hydride (21.61 mg, 0.9005 mmol), and stirred for 10 min. Oxirane, 2,2-dimethyl- (0.4 mL, 4 mmol) was added, and the mixture was heated to 80° C. overnight. The material was extracted with EtOAc, washing with water (3*). The organic layer was concentrated in vacuo to afford the title compound as a brown oil. MS (ES+): m/z=295.06 (100) [MH⁺]. HPLC: t_R=3.29 min (polar_-5 min, ZQ3).

References:

OSI Pharmaceuticals, LLC US2011/281888, 2011, A1 Location in patent:Page/Page column 26

558-30-5 Synthesis

558-30-5
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1H-Pyrazole, 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-

1000801-22-8
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1082503-78-3
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References