Lithium Chloride → HCID 70664468, compound

Temperature

160 °C

5,7-Dichloro-3-(2-chloro-4-fluorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.3 g, 0.61 mmol) was combined with lithium chloride (0.078 g, 1.83 mmol), cesium hydroxide hydrate (0.31 g, 1.83 mmol) and 2-(4-methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.151 g, 0.61 mmol) in 1,4-dioxane (3 mL) and water (0.3 mL) and the mixture was purged with nitrogen. [Tetrakis(triphenylphosphine)]palladium(0) (0.07 g, 0.061 mmol) was added and the mixture was heated in a CEM Discover microwave reactor at 160° C. for 20 minutes. The mixture was allowed to cool and diluted with ethyl acetate then washed with water then brine. The organic layer was concentrated onto silica gel and chromatographed on a silica gel column eluting with 10-35% ethyl acetate in hexanes to give 7-chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-methoxy-3-methylphenyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one.

1. customthe mixture was purged with nitrogen
2. temperatureto cool
3. washthen washed with water
4. concentrationThe organic layer was concentrated onto silica gel
5. customchromatographed on a silica gel column
6. washeluting with 10-35% ethyl acetate in hexanes

ORD record

ord-e8138bf435274d53a0214dae79825e33

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673897B2