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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1193369Generated: October 30, 2026

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66799276, compound

https://huagongshe.com/reaction/1193369

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
ReactantN-Benzyl-N-methylpiperidin-4-amineHCID 1096081—
Reactant5-Bromo-2-methoxypyridineHCID 2734895—
Reactantsodium 2-methylpropan-2-olateHCID 178418730—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
ProductHCID 66799276HCID 6679927636%

Reaction Conditions

Temperature90 °C

Reaction Steps

N-Benzyl-N-methylpiperidin-4-amine (3.947 mmol, 1.0 eq.), 5-bromo-2-methoxypyridine (614 μl, 4.737 mmol, 1.2 eq.) and t-BuONa (757 mg, 7.894 mmol, 2.0 eq.) were dissolved in toluene (12 ml) and degassed with argon. Xantphos (136 mg. 0.237 mmol, 0.06 eq.) and Pd2(dba)3 (72 mg, 0.079 mmol, 0.02 eq.) were then added and the mixture was heated for 4 hours at 90° C. After monitoring by TLC, the reaction mixture was concentrated under reduced pressure and purified by column chromatography (silica gel, 3% MeOH in DCM). Yield: 36% (450 mg, 1.447 mmol)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08680159B2
Source datasetuspto-grants-2014_03
ORD IDord-d0c1c0085d7e44309a0b3be82f39c9a8
Source noteuspto-grants-2014_03