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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200168Generated: November 1, 2026

Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → HCID 66802105, compound

https://huagongshe.com/reaction/2200168

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 4642098—
Reactant1-Bromo-3-nitro-5-(trifluoromethyl)benzeneHCID 7015411—
CatalystHCID 178418397HCID 178418397—
Solvent1,4-DioxaneHCID 31275—
SolventSodium BicarbonateHCID 516892—
ProductHCID 66802105HCID 66802105128.1%

Reaction Conditions

Temperature120 °C

Reaction Steps

Mix 1-bromo-3-nitro-5-(trifluoromethyl)benzene (200 mg, 0.65 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate (175 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.03 mmol) in dioxane and saturated sodium bicarbonate solution (3:1, 10 mL), stir the mixture at 120° C. for 1.5 hrs. Cool to room temperature; concentrate under reduced pressure to give the crude product. Purify by flash chromatography (silica gel, EtOAc:PE=20:1) to afford the product as a yellow solid (310 mg, 82.8%). MS: (M+23): 395.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359338B2
Source datasetuspto-grants-2016_06
ORD IDord-2e144ff24c2748acb1115e347ba7bff1
Source noteuspto-grants-2016_06