5-Benzyl 3-methyl 1-(p-fluorophenyl)-4-isopropyl-1H-pyrazole-3,5-dicarboxylate → 1-(4-fluoro-phenyl)-4-isopropyl-1 H-pyrazole-3,5-dicarboxylic acid 3-methyl ester

HRID 268633Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([C:13]([O:15]CC2C=CC=CC=2)=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]([CH3:12])[CH3:11])=[C:8]([C:13]([OH:15])=[O:14])[N:7]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:6]=1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1-(4-fluoro-phenyl)-4-isopropyl-1H-pyrazole-3,5-dicarboxylic acid 5-benzyl ester 3-methyl ester (18.95 g, 47.8 mmol) in MeOH (300 mL) at 25° C. under N2 was added 10% Pd—C (700 mg; commercially available from Sigma Aldrich). The reaction vessel was evacuated and filled with H2 and then stirred at 25° C. for 3 hrs. Subsequently, the reaction vessel was flushed with N2 and filtered through a pad of celite. The filtrate was concentrated to afford 1-(4-fluoro-phenyl)-4-isopropyl-1H-pyrazole-3,5-dicarboxylic acid 3-methyl ester (14.6g, 99%) in sufficient purity for use in the next step: H-NMR (CDCl3) δ 7.36-7.31 (m, 2 H), 7.11-7.06 (m, 2 H), 3.90 (s, 3 H), 3.86-3.82 (m, 1 H), 1.43 (d, 6 H).

Workup

customThe reaction vessel was evacuated
additionfilled with H2
customSubsequently, the reaction vessel was flushed with N2
filtrationfiltered through a pad of celite
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-7629e32a9f4b48ebb34568720f9f1a1f
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446121B2

Reaction notes

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