Sodium hydride → 1-(3,5-Dimethylisoxazol-4-ylmethyl)-1H-pyrazole-4-carbaldehyde

HRID 220481Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]1.Cl[CH2:11][C:12]1[C:13]([CH3:18])=[N:14][O:15][C:16]=1[CH3:17]>CN(C)C=O>[CH3:18][C:13]1[C:12]([CH2:11][N:3]2[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[N:4]2)=[C:16]([CH3:17])[O:15][N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Add N,N-dimethylformamide (3 mL) to sodium hydride (0.092 g, 2.29 mmol) and stir at 0° C. Add 1-H-pyrazole-4-carboxaldehyde (0.200 g, 2.08 mmol) and stir at 0° C. for 20 min. Dissolve 4-chloromethyl-3,5-dimethylisoxazole (0.318 g, 2.18 mmol) in N,N-dimethylformamide (4 mL) and add to reaction mixture. Stir reaction at room temperature for 18 hr. Quench with aqueous saturated sodium bicarbonate solution. Add ethyl acetate and separate organic layer. Extract aqueous layer twice with ethyl acetate. Dry combined organic layers (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:hexanes), to give the title preparation (387 mg, 91%). GC-MS: m/z=205 [M+].

Workup

stirringStir
customreaction at room temperature for 18 hr
customQuench with aqueous saturated sodium bicarbonate solution
customAdd ethyl acetate and separate organic layer
customDry
filtrationfilter
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 25:75 to 75:25 ethyl acetate:hexanes)
customto give the title
custompreparation (387 mg, 91%)

Sources & evidence

ORD record: ord-b49960dd7d97476f83026d6423df702e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202873B2

Reaction notes

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