ChemicalBook CAS DataBase List 1-METHYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID

1-METHYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID synthesis

6synthesis methods

Product Name:1-METHYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID
CAS Number:119083-00-0
Molecular formula:C6H5F3N2O2
Molecular Weight:194.11

231285-86-2 Synthesis

Ethyl 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

231285-86-2
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$24.00/100mg

1-METHYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLIC ACID

119083-00-0
73 suppliers
$62.00/250mg

Yield: 94%

Reaction Conditions:

with water;lithium hydroxide in tetrahydrofuran at 0 - 20;

Steps:

Intermediate 65b: I -methyl-5-(trifluoromethyl)pyrazole-4-carboxylic acid
[00618] Intermediate 65b: I -methyl-5-(trifluoromethyl)pyrazole-4-carboxylic acid[00619] To a solution of ethyl 1 -methyl-5-(trifluoromethyl)pyrazole-4-carboxylate (2.91 g, 13.Ogmmol) in THF (52mL) at 0 °Cwas added a solution of lithium hydroxide (627mg, 26.l8mmol) in water (26mL) and the mixture was stirred at room temperature overnight. The mixture was thenacidified to pH 1-2 with 1M HCI and extracted with EtOAc (4 x 5OmL). The combined organic layers were washed with brine (5OmL), dried over Na2SO4, filtered and concentrated in vacuo to give 1- methyl-5-(trifluoromethyl)pyrazole-4-carboxylic acid (2.39g, 12.33mmol, 94% yield) as an off-white solid.1H NMR (CDCI3, 400MHz) O/ppm: 8.02 (1H, 5), 4.13 (3H, q, J= 2.0Hz) exchangeable proton notseen. 19F NMR (CDCI3, 400MHz) O/ppm: -57.2.MS Method 2: RT: 1.16 mi mlz 193.0 [M-H]

References:

REDX PHARMA PLC;ARMER, Richard;BELFIELD, Andrew;BINGHAM, Matilda;JOHNSON, Alice;MARGATHE, Jean-Francois;AVERY, Craig;HUGHES, Shaun;MORRISON, Angus WO2016/51193, 2016, A1 Location in patent:Paragraph 00615; 00618; 00619