Water → 5-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide

https://huagongshe.com/reaction/1948557

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine	HCID 2734656	—
Reactant	HCID 45725783	HCID 45725783	—
Catalyst	HCID 178418807	HCID 178418807	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	5-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide	HCID 58408411	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

A solution of 1-2 (100 mg, 0.210 mmol, 1.0 equiv) in THF (2 ml) in a microwave vial was treated with pyridine-3-boronic acid pinacol ester (47.4 mg, 0.231 mmol, 1.1 equiv), cesium carbonate (163 mg, 0.500 mmol, 2.4 equiv), PdCl2(dppf)-CH2Cl2 adduct (17.15 mg, 0.021 mmol, 0.1 equiv), and 0.5 mL water. The mixture was heated to 120° C. in a microwave reactor for 10 min. The mixture was cooled to RT and diluted with EtOAc. The mixture was washed with sat. aq. NH4Cl, dried over Na2SO4, filtered and concentrated. The crude material (1-3) was used as is in the next step. ESI+ MS [M+H]+ C21H19BrN2O3: 428.0 found, 427.3 required.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08399494B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-882cae3045aa497caca54eac90add8d7
Source note	uspto-grants-2013_03