Bromobenzene → HCID 178513764, compound

Temperature

80 °C

3-Amino-1H-pyrazole-4-carboxamide (19.8 g, 157 mmol), K3PO4 (66.7 g, 314 mmol), bromobenzene (23.2 mL, 220 mmol) and 2-propanol (785 mL) were combined in a round bottom flask and purged with a stream of N2 gas for 40 minutes. Pd2(dba)3 (1.80 g, 1.96 mmol) and 2-di-t-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-tri-i-propylbiphenyl (3.77 g, 7.85 mmol) were added and the reaction was purged for an additional 5 minutes. The reaction mixture was then heated to 80° C. and allowed to stir under a N2 atmosphere for 12 hours. The mixture was then allowed to cool to ambient temperature for an additional 16 hours. The reaction mixture was diluted with EtOAc (300 mL) and filtered through celite (slowly). The celite was washed with EtOAc (300 mL) and the combined filtrates were concentrated in vacuo to afford an oil which was purified by MPLC on silica gel (using a gradient elution of 0-10% MeOH/DCM). The major, low rf product, was isolated to afford a reddish-brown oily solid. The brown solid was suspended in 40 mL of warm MeOH, cooled to ambient temperature, and water (40 mL) was added. The mixture was stirred for 30 minutes and filtered. The solid was suction dried for 16 hours to afford the title compound as a peach-colored solid.

1. custompurged with a stream of N2 gas for 40 minutes
2. customthe reaction was purged for an additional 5 minutes
3. temperatureto cool to ambient temperature for an additional 16 hours
4. additionThe reaction mixture was diluted with EtOAc (300 mL)
5. filtrationfiltered through celite (slowly)
6. washThe celite was washed with EtOAc (300 mL)
7. concentrationthe combined filtrates were concentrated in vacuo
8. customto afford an oil which
9. customwas purified by MPLC on silica gel (
10. washa gradient elution of 0-10% MeOH/DCM)
11. customThe major, low rf product, was isolated
12. customto afford a reddish-brown oily solid
13. temperaturecooled to ambient temperature
14. stirringThe mixture was stirred for 30 minutes
15. filtrationfiltered
16. customdried for 16 hours

ORD record

ord-01739f88c5614e27a998ea735769184d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328099B2