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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1427084Generated: November 2, 2026

Cesium carbonate → Methyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-2-fluoro-benzoyl]amino]-2,4-dimethyl-benzoate

https://huagongshe.com/reaction/1427084

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
ReactantTert-butyl-dimethyl-(3-piperidylmethoxy)silaneHCID 58992622—
ReactantMethyl 3-[(5-bromo-2-fluoro-benzoyl)amino]-2,4-dimethyl-benzoateHCID 86707315—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
ProductMethyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-2-fluoro-benzoyl]amino]-2,4-dimethyl-benzoateHCID 86707316—

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of methyl 3-[(5-bromo-2-fluoro-benzoyl)amino]-2,4-dimethyl-benzoate (0.7 g, 1.84 mmol), tert-butyl-dimethyl-(3-piperidylmethoxy)silane (2.53 g, 11.03 mmol, see preparation 14) and Cs2CO3 (1.81 g, 5.50 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.168 g, 0.184 mol) followed by S-Phos (0.075 g, 0.184 mol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 120° C. After 6 hours, the reaction mixture is concentrated under reduced pressure and residue is carried forward without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08933098B2
Source datasetuspto-grants-2015_01
ORD IDord-2b1d73ca060e4ea0a83f2e96c9a478fa
Source noteuspto-grants-2015_01