Sodium Carbonate → 1-Chloro-4-phenyl-5,6,7,8-tetrahydrophthalazine

Temperature

80 °C

1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.270 g, 0.369 mmol), phenylboronic acid (0.900 g, 7.38 mmol) and 1,4-dichloro-5,6,7,8-tetrahydrophthalazine (2.25 g, 11.1 mmol) were combined in a 150 mL sealable vessel under argon. 15 mL dioxane and 2.0 M Sodium carbonate, aqueous (7.38 ml, 14.8 mmol) were added. The vessel was sealed and heated to 80° C. to give a homogenous brown reaction. After 30 min, the reaction was cooled to ambient temperature and was diluted with EtOAc, water, and brine. The layers were separated, and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a red solid. This was taken up in dichloromethane and purified by silica gel chromatography (0-60% EtOAc in hexanes) to give 1-chloro-4-phenyl-5,6,7,8-tetrahydrophthalazine as an off-white solid. MS m/z=245 [M+H]+. Calc'd for C14H13ClN2: 244.7.

1. customThe vessel was sealed
2. customto give
3. customa homogenous brown reaction
4. temperaturethe reaction was cooled to ambient temperature
5. customThe layers were separated
6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a red solid
10. custompurified by silica gel chromatography (0-60% EtOAc in hexanes)

ORD record

ord-d85b23d3497d4663a029c704566009b8

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560551B2