Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 897211Generated: October 30, 2026

Nitrogen → HCID 73712349, compound

https://huagongshe.com/reaction/897211

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantCesium carbonateHCID 10796—
Reactant(3-Chlorophenyl)boronic acidHCID 2734323—
Reactant6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 73712352—
SolventDimethoxyethane ethanol waterHCID 86587095—
ProductHCID 73712349HCID 7371234913.8%

Reaction Conditions

Temperature160 °C

Reaction Steps

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(PPh3)Cl2 (about 1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). 3-Chlorophenyl boronic acid (6.3 mg, 0.046 mmol) was added and the solution was heated in the microwave for 5 minutes at 160° C., filtered, and was purified by Prep HPLC to give 3 mg (11%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 469 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.84-1.91 (m, 2H), 2.25 (br d, 2H), 3.16-3.23 (m, 2H), 3.61 (br d, 2H), 3.84-4.01 (m, 3H), 5.43 (s, 1H), 6.37-6.43 (m, 1H), 6.89 (d, 1H), 7.34-7.94 (m. 12H), 8.41 (d, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06921821B2
Source datasetuspto-grants-2005_07
ORD IDord-b13d743577304cdc9349665a08cbab35
Source noteuspto-grants-2005_07