Potassium Phosphate, Tribasic → HCID 70981716, compound

Temperature

90 °C

Into a flask containing a solution of benzyl 2-bromo-1-methyl-1H-imidazole-4-carboxylate (2 g, 6.77 mmol) in 1,2-dimethoxyethane (40 ml), potassium phosphate (2.3 g, 20.3 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.41 g, 6.77 mmol) were added at RT under argon atmosphere. The resulting mixture was degassed and purged with argon for 10 minutes. Then Pd(PPh3)4 (0.310 g, 0.2 mmol) was added to the reaction mixture and heated at 90° C. for 12 h. The reaction mixture was filtered through a celite bed and the filtrate was diluted with water and extracted with EtOAc. The organic layer was concentrated and purified by flash chromatography. Yield 1.1 g. 1H-NMR (400 MHz; CDCl3): δ 3.77 (s, 3H), 3.95 (s, 3H), 5.36 (s, 2H), 7.30-7.37 (m, 3H), 7.45 (d, 2H), 7.59 (s, 1H), 7.79 (s, 1H), 7.89 (s, 1H).

1. additionwere added at RT under argon atmosphere
2. customThe resulting mixture was degassed
3. custompurged with argon for 10 minutes
4. filtrationThe reaction mixture was filtered through a celite bed
5. additionthe filtrate was diluted with water
6. extractionextracted with EtOAc
7. concentrationThe organic layer was concentrated
8. custompurified by flash chromatography

ORD record

ord-b375d6a9973b43fe9d85241114e53f4e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921378B2