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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 640163Erstellt: 23. Oktober 2026

Tri-o-tolylphosphine → 3-(4-(4-Benzyloxy-benzyl)-pyrazol-1-yl)-pyridin-2-ylamine

https://huagongshe.com/de/reaction/640163

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTri-o-tolylphosphineHCID 80271—
Edukt3-(4-Bromo-pyrazol-1-yl)-pyridin-2-ylamineHCID 59255090—
Edukt(4-Benzyloxy-benzyl)-tributyl-stannaneHCID 59255482—
Katalysatorpalladium(II) acetateHCID 167845—
LösungsmittelN-methyl-2-pyrrolidoneHCID 13387—
Produkt3-(4-(4-Benzyloxy-benzyl)-pyrazol-1-yl)-pyridin-2-ylamineHCID 592554415,2%

Reaktionsbedingungen

Temperatur120 °C

Reaktionsschritte

To a mixture of 3-(4-bromo-pyrazol-1-yl)-pyridin-2-ylamine (34 mg, 0.14 mmol) described in Manufacturing Example 39-1-4, (4-benzyloxy-benzyl)-tributyl-stannane (84 mg, 0.17 mmol) described in Manufacturing Example 39-2-1 and N-methylpyrrolidinone (1.5 mL) were added tri-o-tolylphosphine (17 mg, 0.057 mmol) and palladium (II) acetate (3.2 mg, 0.014 mmol) at room temperature, which was stirred for 5 hours at 120° C. The reaction mixture was cooled to room temperature, and filtered after addition of an aqueous potassium fluoride solution and ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid) to obtain the title compound (2.6 mg, 4%) as a trifluoroacetic acid salt.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07691882B2
Quelldatensatzuspto-grants-2010_04
ORD IDord-5c8491e7d131409a9a810cd1d6a61ede
Quellennotizuspto-grants-2010_04