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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204744Generated: October 31, 2026

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

https://huagongshe.com/reaction/2204744

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}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamideHCID 66611954—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
Product2-{[(2,4-Difluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamideHCID 66611764—

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide (may be prepared as described in Example 9; 162 mg, 0.31 mmol) in 1,2-dimethoxyethane (5 ml) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (78 mg, 0.38 mmol), Pd(Ph3P)4 (21.67 mg, 0.02 mmol) and sodium carbonate (0.63 ml, 0.63 mmol). The mixture was heated at 120° C. in the microwave for 35 minutes, cooled and the solvent removed in vacuo. Purification by MDAP yielded the title compound as a brown solid. 75 mg.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365551B2
Source datasetuspto-grants-2016_06
ORD IDord-bbcf66b2b2fe4f73865956d01e8b2807
Source noteuspto-grants-2016_06