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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 417396Erstellt: 23. Oktober 2026

Sodium Bicarbonate → 2-(5-{7-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-9,10-dihydro-phenanthren-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/de/reaction/417396

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSodium BicarbonateHCID 516892—
Edukt4,4,5,5-Tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,10-dihydro-phenanthren-2-yl]-[1,3,2]dioxaborolaneHCID 58789476—
EduktHCID 178451675HCID 178451675—
KatalysatorHCID 178418397HCID 178418397—
LösungsmittelWaterHCID 962—
Lösungsmittel1,2-DimethoxyethaneHCID 8071—
Produkt2-(5-{7-[2-(1-Boc-pyrrolidin-2-yl)-3H-imidazol-4-yl]-9,10-dihydro-phenanthren-2-yl}-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 6662121024%

Reaktionsbedingungen

Temperatur80 °C

Reaktionsschritte

Pd(PPh3)4 (31 mg, 0.03 mmol) was added to a mixture 4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,10-dihydro-phenanthren-2-yl]-[1,3,2]dioxaborolane (115 mg, 0.27 mmol), 2-(4-bromo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (173 mg, 0.55 mmol), NaHCO3 (159 mg, 1.9 mmol) in 1,2-dimethoxyethane (5 mL) and water (1 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 6 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product as a white solid (42 mg, 24%). m/z 651.0 (M+H)+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08088368B2
Quelldatensatzuspto-grants-2012_01
ORD IDord-68e399114b9742249fdbf56a000e55ec
Quellennotizuspto-grants-2012_01