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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 573617Generated: October 31, 2026

1-Methylimidazole → 3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

https://huagongshe.com/reaction/573617

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylimidazoleHCID 1390—
ReactantN-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamideHCID 53250396—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178511492HCID 178511492—
Product3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamideHCID 6832407231.5%

Reaction Steps

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (85 mg, 0.162 mmol) (Example 33), potassium ferrocyanide (13.71 mg, 0.032 mmol), copper(I) iodide (3.09 mg, 0.016 mmol) in 1-methylimidazole (1 mL, 12.55 mmol) was subjected to microwave reaction at 160° C. for 1 h. Purification by chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in cyclohexane, afforded the title compound (24 mg). LCMS (A) m/z: 470 [M+1]+, Rt 1.58 min (acidic), Rt 1.09 min (basic).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09029545B2
Source datasetuspto-grants-2015_05
ORD IDord-56f80372eee3410eaea15a3f5da8e19d
Source noteuspto-grants-2015_05