Sodium Iodide → 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate

HRID 2283757

Reaction equation

[C:1]([O-:4])(=[O:3])[CH3:2].[K+].[I-].[Na+].CN(C=O)C.[Br:13][C:14]1[C:15]([C:26]#[N:27])=[N:16][N:17]([CH2:24][CH3:25])[C:18]=1[CH2:19][CH2:20][CH2:21][CH2:22]Cl>O>[C:1]([O:4][CH2:22][CH2:21][CH2:20][CH2:19][C:18]1[N:17]([CH2:24][CH3:25])[N:16]=[C:15]([C:26]#[N:27])[C:14]=1[Br:13])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium acetate (1.69 g, 17.2 mmol), sodium iodide (255 mg, 1.7 mmol), and DMF (17 mL) were added to 4-bromo-5-(4-chlorobutyl)-1-ethyl-1H-pyrazole-3-carbonitrile (1.0 g, 3.4 mmol, prepared as described in Parts A-E of Example 19), and the reaction was heated at 100° C. for two hours under a nitrogen atmosphere and allowed to cool to ambient temperature. Water was added, and the resulting mixture was extracted with diethyl ether. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge, eluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40) to provide 0.86 g of 4-(4-bromo-5-cyano-2-ethyl-2H-pyrazol-3-yl)butyl acetate.

Workup

temperatureto cool to ambient temperature
extractionthe resulting mixture was extracted with diethyl ether
washThe combined extracts were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge
washeluting with hexanes/ethyl acetate in a gradient from 90:10 to 60:40)

Sources & evidence

ORD record: ord-ccbbcce73c014a1791d3fa6e720f7fcb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145410B2

Linked notes

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