A common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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. 35277-02-2.
A mixture of tert-butyl 4-[[2-[5-bromo-3-(methoxymethoxy)-2-pyridyl]thiazolo[5,4-d]thiazol-5- yl]-methyl-amino]piperidine-l-carboxylate (86 mg, 0.15 mmol), obtained using the chemistry described in Example 16, Step 2, 4-fluoro-lH-pyrazole (19 mg, 0.22 mmol), cuprous iodide (3 mg, 0.016 mmol), trans-N,N’-dimethylcyclohexane-l, 2-diamine (5 mg, 0.034 mmol) and K2CO3 (52 mg, 0.38 mmol) in toluene (0.3 mL) was stirred at 100 C for 12 h. The reaction was concentrated, diluted with CH2CI2 and washed with aqueous NH4CI, brine and dried. After the removal of the solvent, the residue was chromatographed (EtOAc in CH2CI2, 0-100%) to provide tert-butyl 4- [ [2- [5-(4-fluoropyrazol- 1 -yl)-3 -(methoxymethoxy)-2-pyridyl] thiazolo [5 ,4-d] thiazol- 5-yl]-methyl-amino]piperidine-l-carboxylate. The product was treated with HC1 in dioxane (3.0 mL, 4.0 M) at room temperature for 4 h and the precipitate was collected, wahsed with diethyl ether and dried to provide 5-(4-fluoropyrazol-l-yl)-2-[5-[methyl(4-piperidyl)amino]thiazolo[5,4- d]thiazol-2-yl]pyridin-3-ol hydrochloride (46 mg, 65.2%). LC-MS 432.4 [M+H]+, RT 1.21 min, 1H NMR (DMSO -d6) d: 11.15 (br s, 1H), 8.69-8.94 (m, 3H), 8.65 (d, 7=2.1 Hz, 1H), 7.97 (d, 7=4.0 Hz, 1H), 7.86 (d, 7=2.1 Hz, 1H), 4.37-4.62 (m, 1H), 3.33- 3.42 (m, 2H), 3.04-3.19 (m, 2H), 3.01 (s, 3H), 2.03-2.18 (m, 2H), 1.84-1.97 (m, 2H).
The synthetic route of 4-Fluoro-1H-pyrazole has been constantly updated, and we look forward to future research findings.