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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1039640Generated: November 2, 2026

Dimethylformamide → N-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamide

https://huagongshe.com/reaction/1039640

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantCesium carbonateHCID 10796—
Reactant(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonateHCID 18649743—
ReactantN-((R)-5-Bromoindan-2-yl)-5-hydroxypyridine-2-carboxamideHCID 66679915—
SolventWaterHCID 962—
ProductN-((R)-5-bromoindan-2-yl)-5-[(S)-1-(tetrahydrofuran-2-yl)methoxy]pyridine-2-carboxamideHCID 66679917—

Reaction Conditions

Temperature60 °C

Reaction Steps

A mixture of N-((R)-5-bromoindan-2-yl)-5-hydroxypyridine-2-carboxamide (1.50 g), (S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate (0.81 g), cesium carbonate (1.46 g) and DMF (20 ml) was heated to 60° C. for 4 hours. The cooled reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was washed three times with water, dried over magnesium sulfate and concentrated. This afforded the product with the molecular weight of 417.31 (C20H21BrN2O3); MS (ESI): 417 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08552199B2
Source datasetuspto-grants-2013_10
ORD IDord-582578daa5ef4a2a8803afc8f6716584
Source noteuspto-grants-2013_10