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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2175953Generated: October 31, 2026

3-Methyl-2-(tributylstannyl)pyridine → Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate

https://huagongshe.com/reaction/2175953

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Methyl-2-(tributylstannyl)pyridineHCID 16427098—
ReactantMethyl 3-bromo-6-methylpyridine-2-carboxylateHCID 90404668—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
ProductMethyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylateHCID 9041213518.9%

Reaction Conditions

Temperature150 °C

Reaction Steps

To the title compound of step B (509 mg, 2.2 mmol) and the title compound of step C (1.1 g, 2.9 mmol) in PhCH3 (6.6 mL) was added Pd(PPh3)4 (225 mg, 0.2 mmol). The reaction was degassed with N2 and heated at 150° C. for 1.5 h using microwave reactor. The reaction was cooled to rt, diluted with H2O and extracted with EtOAc. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-100% EtOAc in heptane) gave the title compound (101 mg, 18%). MS (ESI) mass calcd. for C14H14N2O2, 242.3; m/z found 243 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09062078B2
Source datasetuspto-grants-2015_06
ORD IDord-8354ce1514984632a8d94ed947c04494
Source noteuspto-grants-2015_06