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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2201144Generated: October 29, 2026

m-Toluidine → HCID 69284811, compound

https://huagongshe.com/reaction/2201144

Reaction equation

Participants

RoleNameHCIDCharge
Reactantm-ToluidineHCID 7934—
ReactantCesium carbonateHCID 10796—
ReactantBinap, (A+-)-HCID 634876—
ReactantHCID 86666164HCID 86666164—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 69284811HCID 6928481177.4%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of (S)-benzyl 1-(1-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)propyl)cyclopropylcarbamate (60 mg, 0.15 mmol) in dioxane (1 mL) was added m-toluidine (19 mg, 0.18 mmol), BINAP (18.7 mg, 0.03 mmol), Pd(OAc)2 (6.7 mg, 0.03 mmol) and Cs2CO3 (146 mg, 0.45 mmol). After degassed with Argon, the mixture was heated at 80° C. for 15 h. The mixture was diluted with dioxane, precipitate was filtered off, filter cake was washed with ACN, the filtrate was concentrated and purified by column to give of (S)-benzyl 1-(1-(5-cyano-3-fluoro-6-(m-tolylamino)pyridin-2-ylamino)propyl)cyclopropylcarbamate (55 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359375B2
Source datasetuspto-grants-2016_06
ORD IDord-48785cd2657a450aa826b5a8e2d5c41b
Source noteuspto-grants-2016_06