Electric Literature of 942853-22-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 942853-22-7 name is 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Compound 1029; Starting material Ai (45 mg, 0.056 mmol) is dissolved in 4 N HCI/dioxane and the reaction mixture is for 1 h at RT. The reaction mixture is concentrated in vacuo to give crude Ci. The acid R2i is dissolved in DMF (2.0 mL), DIPEA (0.059 mL, 0.338 mmol) and TBTU (21 .7 mg, 0.068 mmol) are added. The reaction mixture is stirred for 15 mins. The crude Ci is added and the reaction mixture is stirred at RT for 16 h. The reaction mixture is purified by prep HPLC to provide compound 1029. FIA M.S.(electrospray) : 874.4 (M+H)+ Retention time (min) = 6.0 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1 H) , 8.92 (s, 1 H), 7.95 (b, 1 H), 7.93 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 9.0 Hz), 7.08 (d, 1 H, J = 9.4 Hz), 6.74 (d, 1 H, J = 2.3 Hz), 6.40 (s, 1 H), 5.60 (b, 1 H), 5.44 (m, 1 H), 5.23 (q, 2H, J = 9.3 Hz), 5.09 (b, 1 H), 4.63 (b, 1 H), 4.47 (q, 2H, J = 6.9 Hz), 4.43 (b, 2H), 4.04 (b, 1 H), 3.87 (s, 3H), 2.67-2.65 (m, 1 H), 2.43 (s, 3H), 2.38-2.32 (m, 3H), 2.01 -1 .80 (m, 2H), 1 .58-1 .51 (m, 3H), 1 .44-1 .23 (m, 1 1 H), 1 .39 (t, 3H, J = 7.0 Hz), 0.85 (b, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,2,2-Trifluoroethyl)-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.
Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics