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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 253124Generated: October 29, 2026

Toluene → HCID 66844924, compound

https://huagongshe.com/reaction/253124

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant2-Fluorophenylboronic acidHCID 2734354—
ReactantHCID 86614017HCID 86614017—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
ProductHCID 66844924HCID 6684492453.6%

Reaction Steps

To a microwave tube was added methyl-3-methyl-5-oxo-6-(trifluoromethylsulfonyloxy)-1,2,3,5-tetrahydroindolizine-8-carboxylate (94 mg, 0.26 mmol), 2-fluorophenylboronic acid (37 mg, 0.26 mmol, Aldrich), and 2 M sodium carbonate (0.65 mL, 1.30 mmol). To this was added 4 mL of toluene, 0.25 mL of EtOH, and Pd(PPh3)4 (20 mg, 0.17 mmol, Aldrich). The tube was sealed and treated in Emry's optimizer for 15 min at 160° C. The aqueous phase was separated and acidified to pH 2 with 2 N HCl and extracted with EtOAc (3×). The combined EtOAc layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 40 mg (53%) of the title compound as a light brown residue. MS m/z: 288.1(M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07872009B2
Source datasetuspto-grants-2011_01
ORD IDord-a81f4b0bd48c4523b1efcab3a448e13b
Source noteuspto-grants-2011_01