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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1843701Generated: November 1, 2026

1,10-Phenanthroline → Methyl 3-({6-[(5-chloro-3-bromopyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoate

https://huagongshe.com/reaction/1843701

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,10-PhenanthrolineHCID 1318—
ReactantCesium carbonateHCID 10796—
Reactant3-Bromo-5-chloro-2-fluoropyridineHCID 40427010—
ReactantMethyl 3-[(6-hydroxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzoateHCID 56933238—
CatalystCopper iodideHCID 83717—
SolventDimethylformamideHCID 6228—
ProductMethyl 3-({6-[(5-chloro-3-bromopyridin-2-yl)oxy]-1-methyl-1H-benzimidazol-2-yl}methoxy)benzoateHCID 6670585391%

Reaction Steps

The reaction and post-treatment were carried out according to Example (1f) using methyl 3-[(6-hydroxy-1-methyl-1H-benzimidazol-2-yl)methoxy]benzoate produced in Example (1e) (9.40 g, 30.0 mmol), 3-bromo-5-chloro-2-fluoropyridine (6.90 g, 33.0 mmol), copper iodide (0.57 g, 3.00 mmol), 1,10-phenanthroline (0.54 g, 3.00 mmol), cesium carbonate (29.3 g, 90 mmol) and DMF (90 mL) to obtain the title compound (13.7 g, 91%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946264B2
Source datasetuspto-grants-2015_02
ORD IDord-dc9bee972427480aaa2ddd791066996d
Source noteuspto-grants-2015_02