Water → 3-(4-isopropoxyphenyl)-1-(2-methoxyethyl)-1H-pyrazole-4-carbaldehyde

HRID 526775Notes

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([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][O:28][CH3:29].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]([CH2:26][CH2:27][O:28][CH3:29])[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 (655 mg, 4.6 mmol) in acetonitrile (6 ml) was stirred at 0-5° C. for 1 hr. 1-bromo-2-methoxyethane (195 mg, 1.4 mmol) was added and the reaction mixture was 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 was washed with brine (100 mL), dried and concentrated under vacuum (360 mg, yield 72%). The crude material was used in the next step without purification.

Workup

stirringthe reaction mixture was stirred at ambient temperature for 48 h
extractionextracted with EtOAc (50 mL×3)
washThe combined extracts was washed with brine (100 mL)
customdried
concentrationconcentrated under vacuum (360 mg, yield 72%)
customThe crude material was used in the next step without purification

Sources & evidence

ORD record: ord-805567eaa43440158fbc452578a633a7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346761B2

Reaction notes

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