1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyra Zole

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is a pyrazole boronic ester widely used as a building block in pharmaceutical synthesis. 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a key intermediate in the preparation of 1-methyl-1H-pyrazol-4-yl derivatives and is extensively used in the synthesis of kinase inhibitors and other bioactive molecules via Suzuki-Miyaura cross-coupling. 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is a crucial intermediate in drug discovery, enabling rapid SAR exploration around the pyrazole core. Additionally, 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is valuable for generating diverse compound libraries and constructing carbon-carbon bonds in complex molecule synthesis.

 
Product Parameters

Application

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole is a reagent used in pharmaceutical synthesis, including the preparation of selective and orally bioavailable LRRK2 inhibitors for the treatment of Parkinson's disease.

Synthetic Route

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.40 g, 2.06 mmol) in tetrahydrofuran (THF, 10 mL), sodium hydride (NaH, 60% dispersion in mineral oil) was added at 0°C. Subsequently, iodomethane (0.25 mL, 4.12 mmol) was added slowly. The reaction mixture was stirred at room temperature for 4 hours. After the reaction was completed, the reaction was quenched with saturated ammonium chloride (NH4Cl, 20 mL) solution, and extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine (20 mL), and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to afford 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 108, 0.40 g, yield 93.00%) as a yellow viscous liquid. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 1.31 (s, 12H), 3.91 (s, 3H), 7.65 (s, 1H), 7.77 (s, 1H). LCMS (Method-D) analysis showed a retention time of 1.58 minutes, [M+1] 209.1

Storage Conditions

Store 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in a tightly sealed container at +4°C (refrigerator), protected from moisture and light. The compound is moisture-sensitive and should be handled under inert atmosphere when possible. Allow the sealed container to reach ambient temperature before opening to minimize moisture condensation. Keep away from strong oxidizing agents and strong acids.

Shelf life: 2–3 years when stored at +4°C in a sealed, dry container. Stability data are available upon request.

Handling precautions: Use in a fume hood. Wear chemical-resistant gloves, safety goggles, and a lab coat. Avoid generating dust or aerosols. Handle under inert atmosphere when possible. After handling, wash hands thoroughly. Refer to the Safety Data Sheet (SDS) for complete safety information.

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