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5-METHYL-2-PHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID synthesis

6synthesis methods
-

Yield: 97.6%

Reaction Conditions:

with water;sodium hydroxide in tetrahydrofuran;methanol at 25; for 12 h;

Steps:

89; 154
[0894] to a solution of compound 149a (700.0 mg, 3.04 mmol) in THF (20 ml) and MeOH (20ml) was added NaOH (2m, 30) .the mixture was stirred at 25 °C for 12 hours. The mixture was concentrated, diluted with H2O (20 ml), extracted with ethyl acetate (20 ml), the water phase was added HCl (1m) until ph ~ 1, then the mixture was extracted with ethyl acetate (20 ml), the organic layer was washed with brine (20 ml), dried over Na2SO4 and concentrated. Compound 149c (600.0 mg, yield 97.6%) was obtained as a colorless oil. 1H NMR (400mhz, DMSO-d6) δ 13.21 (br s, 1h), 7.49 - 7.31 (m, 5h), 6.81 (s, 1h), 2.24 (s, 3h).

References:

BLADE THERAPEUTICS, INC.;BUCKMAN, Brad, Owen;YUAN, Shendong;ADLER, Marc;EMAYAN, Kumaraswamy;MA, Jingyuang WO2018/64119, 2018, A1 Location in patent:Paragraph 0894; 1307

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