Cerium(III) chloride → 3-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopent-2-enol

Temperatur

0 °C

A suspension of 3-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cyclopent-2-enone (2125 mg, 5.37 mmol) and cerium (iii) chloride (1325 mg, 5.37 mmol) in tetrahydrofuran (300 mL) and methanol (30.0 mL) was cooled to 0° C. under nitrogen. Sodium borohydrate (813 mg, 21.50 mmol) was added in 4 lots over 20 min. The reaction was warmed to 23° C. over 2 h. After a total reaction time of 4 h, the reaction was quenched with saturated ammonium chloride solution (10 ml, slowly—effervescence). The solution was diluted with EtOAc (500 mL) and washed with saturated ammonium chloride solution (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-8% methanol/dichloromethane), affording the product as a yellow film.

1. temperatureThe reaction was warmed to 23° C. over 2 h
2. customAfter a total reaction time of 4 h, the reaction was quenched with saturated ammonium chloride solution (10 ml
3. additionThe solution was diluted with EtOAc (500 mL)
4. washwashed with saturated ammonium chloride solution (100 mL) and brine (100 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. custompurified by silica gel chromatography (eluant: 1-8% methanol/dichloromethane)
8. customaffording the product as a yellow film

ORD-Eintrag

ord-1e7816eab4f94e2db15a1379ce9bb402

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08759532B2