Benzyl Bromide → Ammonium Hydroxide

Temperature

50 °C

A mixture of 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.10 g, 0.189 mmol) and benzyl bromide (0.036 g, 0.208 mmol) in CH3CN (1 mL) was heated at 50° C. for 18 h. The solvent was removed in vacuo and the residue was heated to reflux in MeOH (3 mL) for 1 h, then concentrated under reduced pressure. The residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL). The organic layer was removed and the aqueous phase extracted further with CH2Cl2 (2×3 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with CH2Cl2 ; 4% MeOH; 0.4% NH4OH, to give the title compound:

1. customThe solvent was removed in vacuo
2. temperaturethe residue was heated
3. temperatureto reflux in MeOH (3 mL) for 1 h
4. concentrationconcentrated under reduced pressure
5. customThe residue was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (3 mL)
6. customThe organic layer was removed
7. extractionthe aqueous phase extracted further with CH2Cl2 (2×3 mL)
8. dry with materialThe combined organic extracts were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash column chromatography
12. washeluting with CH2Cl2

ORD record

ord-1fcb1bfd4a084dfe9069b45a64d41945

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05939439