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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2090393Generated: November 2, 2026

Methyl iodide → 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

https://huagongshe.com/reaction/2090393

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantTetrahydrofuranHCID 8028—
ReactantPotassium tert-butoxideHCID 23665647—
ReactantHCID 178431094HCID 178431094—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2760077—

Reaction Steps

Potassium tert-butoxide in THF (1.0 M, 0.309 mL, 0.309 mmol) was added to a solution of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (30.0 mg, 0.155 mmol, Alfa Aesar, Cat. No. H27619) in DMF (0.5 mL) and stirred at r.t. for 10 min, and then methyl iodide (28.9 uL, 0.464 mmol) was added and the stirred at r.t. for 1 h. LCMS showed the reaction was complete. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated to give the crude product which was directly used in the next reaction without further purification. LCMS (M+H−82)+: m/z=127.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08436008B2
Source datasetuspto-grants-2013_05
ORD IDord-1c621b4d8a104c539f4274238cf8127d
Source noteuspto-grants-2013_05