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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204746Generated: October 31, 2026

Sodium Carbonate → 2-{[(2,4-Difluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylmethyl)benzamide

https://huagongshe.com/reaction/2204746

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2773987—
Reactant5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-4-(4-morpholinylmethyl)benzamideHCID 66610654—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
Product2-{[(2,4-Difluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylmethyl)benzamideHCID 66611699—

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-4-(4-morpholinylmethyl)benzamide (may be prepared as described in Example 21; 89 mg, 0.18 mmol) in 1,2-dimethoxyethane (3 ml) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (40.4 mg, 0.19 mmol), sodium carbonate (0.35 ml, 0.35 mmol) and Pd(Ph3P)4 (12.23 mg, 10.59 μmol). The mixture was heated at 120° C. in a microwave for 35 minutes, the solvent removed in vacuo and the residue purified by MDAP to yield the title compound as a white solid. 12 mg.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365551B2
Source datasetuspto-grants-2016_06
ORD IDord-3316d02998d44987ad84ca8e1dcd96a6
Source noteuspto-grants-2016_06