These common heterocyclic compound, 15801-69-1, name is 4-Bromo-1,3,5-trimethyl-1H-pyrazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 4-Bromo-1,3,5-trimethyl-1H-pyrazole
EXAMPLE 62: 7-Fluoro-4-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,4-dihydropyrazolo[4,3-b]indole [0444] 7-Fluoro-l-(tetrahydro-2H-pyran-2-yl)-l,4-dihydropyrazolo[4,3-]indole (40 mg, 0.154 mmol), 4-bromo-l,3,5-trimethyl-lH-pyrazole (29.2 mg, 0.154 mmol), copper(I) iodide (2.94 mg, 0.015 mmol), Cs2C03 (151 mg, 0.463 mmol) and DMF (lmL) were mixed in an 8 mL tube equipped with a magnetic stir bar to give a brown suspension. The solvent was purged with N2 and the tube was sealed and heated in a microwave for 60 minutes at 22C. More 4-bromo-l,3,5-trimethyl-lH-pyrazole (29.2 mg, 0.154 mmol), copper(I) iodide (2.94 mg, 0.015 mmol) and Cs2C03 (151 mg, 0.463 mmol) were added and the mixture was heated for an additional hour. The reaction mixture was subsequently partitioned between water (25 mL) and EtOAc (50 mL). The layers were separated. The organic layer was washed with brine (20 mL), dried over Na2S04, filtered, and concentrated to yield a brown syrup. The residue was dissolved in MeOH (5 mL) and treated with concentrated HC1 (4 drops). The reaction mixture was stirred overnight and the product was purified by preparative HPLC, eluting with 25-50% ACN in water (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a clear glass (7.8 mg, 13%). 1H NMR (400 MHz, DMSO-de) delta ppm 1.88 (s, 3 H), 2.02 (s, 3 H), 3.76 (s, 4 H), 6.95 – 6.99 (m, 2 H), 7.13 (td, J=9.16, 2.65 Hz, 1 H), 7.52 (s, 1 H), 7.61 (dd, J=8.97, 2.40 Hz, 1 H). MS [M+H]+ calc’d for Ci5Hi4FN5, 284.13; found 284.2.
The synthetic route of 4-Bromo-1,3,5-trimethyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.