Analyzing the synthesis route of 25016-11-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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. name: 1-Methyl-1H-pyrazole-4-carbaldehyde

Step 2) Potassium t-butoxide (23.47 g, 199.1 mmol, 2.44 eq.) was suspended in anhydrous DME (90 mL) and cooled to – 60C. Tosyl methyl isocyanide (23.76 g, 121.7 mmol, 1.49 eq.) was dissolved in anhydrous DME (75 mL) and the solution was added drop- wise to the potassium t-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55C, the aldehyde from Step 1 in anhydrous DME (55 mL) was added over 23 minutes. The reaction was stirred for one hour at – 55 to – 50C, and then methanol (90 mL) was added. The cooling bath was removed, and after stirring for 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 mL) with acetic acid (9 mL). This was extracted with ethyl acetate (3 x 250 mL), and these extracts were combined, washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield a bright yellow oil in 63% yield (7.89 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHUMWAY, Stuart Denham; TONIATTI, Carlo; ROBERTS, Brian Scott; MARTIN, Melissa M.; WO2013/39854; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics