Water → 3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazole-4-carbaldehyde

HRID 526770Notes

Reaction equation

Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH:17]=[O:18])=[CH:15][NH:14][N:13]=2)=[CH:8][CH:7]=1)[CH3:4].[C:19]([O-])([O-])=O.[K+].[K+].CI.O>C(#N)C>[CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH:17]=[O:18])=[CH:15][N:14]([CH3:19])[N:13]=2)=[CH:8][CH:7]=1)([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 2.5 °C

Procedure

A mixture of 3-[4-(propan-2-yloxy)-phenyl]-1H-pyrazole-4-carbaldehyde hydrochloride (400 mg, 1.5 mmol) and K2CO3 (624 mg, 4.5 mmol) in acetonitrile (6 mL) was stirred at 0-5° C. for 1 h. Methyl iodide (310 mg, 2.2 mmol) was added and the mixture stirred at ambient temperature for 48 h. The reaction was poured into water (200 mL) and extracted with EtOAc (50 mL×3). The combined extracts were washed with brine (100 mL), dried, and concentrated under vacuum. The residue was purified by prep-TLC using Hexane:EtOAc (210:90) as eluent to afford the 3-(4-isopropoxyphenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (82 mg, Yield: 19%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.94 (s, 1H), 8.00 (s, 1H), 7.68-7.64 (m, 2H), 7.02-6.97 (m, 2H), 4.69-4.59 (t, J=6.0 Hz, 1H), 4.00 (s, 3H), 1.38 (d, J=6.0 Hz, 6H) ppm. LCMS (method C RT=2.08 min, m/z=245.2 [M+H]+.

Workup

stirringthe mixture stirred at ambient temperature for 48 h
extractionextracted with EtOAc (50 mL×3)
washThe combined extracts were washed with brine (100 mL)
customdried
concentrationconcentrated under vacuum
customThe residue was purified

Sources & evidence

ORD record: ord-541db0f55e5643ad995c4348a013fbcb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346761B2

Reaction notes

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