Benzyl Bromide → HCID 118159323, Verbindung

Benzyl bromide was purified by passage through a plug of basic alumina prior to use. A solution of 3-chloro-2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)pyrido[3,4-b]pyrazine (736.2 mg, 1.954 mmol) in ACN (9.77 mL) was divided into two equal portions. Each solution was treated with a half portion of benzyl bromide (232 μL, 1.954 mmol) and stirred at 80° C. for 3 h. The reaction mixtures were allowed to cool to room temperature, and Each solution was treated with a half portion of sodium triacetoxyborohydride (1.242 g, 5.86 mmol). The reaction mixtures were stirred at room temperature for 1 h, then were quenched with saturated aqueous NaCl. The reaction mixtures were combined and partitioned between EtOAc with Et2O added to assist in phase separation and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using a 20% to 60% gradient of EtOAc in heptanes gave the title compound (522.2 mg, 56.8%). ESI-MS m/z [M+H]+ 471.4.

1. customBenzyl bromide was purified by passage through a plug of basic alumina
2. customThe reaction mixtures
3. temperatureto cool to room temperature
4. customThe reaction mixtures
5. stirringwere stirred at room temperature for 1 h
6. customwere quenched with saturated aqueous NaCl
7. customThe reaction mixtures
8. custompartitioned between EtOAc with Et2O
9. additionadded
10. customto assist in phase separation and saturated aqueous NaCl
11. dry with materialThe organic layer was dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified by flash silica gel chromatography

ORD-Eintrag

ord-2f0a7ebad0be4df59849f20a787943d9

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09181249B2