Sodium hydride → (R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

To a solution of (R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (1.0 g, 3.4 mmol) in DMF (5 mL) was added NaH (280 mg, 6.8 mmol) at 0° C. After 0.5 h, 5-chloro-2-fluoropyridine (540 mg, 4.08 mmol) was added. The mixture was stirred at room temperature overnight. After quenching with H2O (30 mL), the reaction mixture was extracted with ethyl acetate (10 mL*3). The organic layer was washed with brine and dried over sodium sulfate. Concentrated in vacuo gave (R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (1.0 g, crude) for the next step directly. LRMS (M+H+)+: calcd 403.02. found 404.01.

1. customAfter quenching with H2O (30 mL)
2. extractionthe reaction mixture was extracted with ethyl acetate (10 mL*3)
3. washThe organic layer was washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationConcentrated in vacuo

ORDレコード

ord-ba3b42f8f54b4b2ea3cdea8619c6f0ef

出典データセット

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09422292B2