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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 923790Generated: November 1, 2026

Dimethylformamide → 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

https://huagongshe.com/reaction/923790

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactanto-FluorobenzaldehydeHCID 67970—
ReactantN2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 2735930—
ReactantSodium BisulfiteHCID 23665763—
SolventWaterHCID 962—
Product2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineHCID 6798184030.2%

Reaction Conditions

Temperature153 °C

Reaction Steps

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (1.91 g), 2-fluorobenzaldehyde (1.86 g), sodium hydrogen sulfite (1.56 g), and DMF (10 ml) was stirred with heating under reflux at 153° C. for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.89 g of 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound (1E)-F1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278983B2
Source datasetuspto-grants-2016_03
ORD IDord-445f888e63a4426687602248aba1553b
Source noteuspto-grants-2016_03