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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1047009Generated: November 1, 2026

Sodium Carbonate → HCID 69087719, compound

https://huagongshe.com/reaction/1047009

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant4-(Methanesulfonyl)phenylboronic acidHCID 2734364—
Reactanttert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamateHCID 136331866—
CatalystBis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)HCID 11714597—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 69087719HCID 69087719—

Reaction Steps

A mixture of tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.097 mmol), [4-(methyl sulfonyl)phenyl]boronic acid (39 mg, 0.20 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg, 0.1 mmol), and 2M Na2CO3 aq. (0.097 mL, 0.20 mmol) in DMF (1.5 mL) was treated with microwave (160° C. for 1 hour). The mixture was diluted with AcOEt, washed with water (×3), brine, dried over Na2SO4, and then filtrated through Celite pad. The filtrate was concentrated and the residue was purified by preparative thin-layer chromatography (n-hexane/AcOEt=1:1×2) to afford the mixture of the desired product and tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl)cyclobutyl}carbamate (51 mg) as a yellow solid. LCMS: 634 [M+H].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08569331B2
Source datasetuspto-grants-2013_10
ORD IDord-34ce6d41aa1f414ea1719d3eb898c10e
Source noteuspto-grants-2013_10