Dimethylformamide → 1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde

Temperature

-78 °C

To a −78° C. solution of 4-bromo-1-(4-methoxyphenyl)-1H-pyrazole (506 mg, 2.0 mmol) in anhydrous tetrahydrofuran (20 mL) was added n-butyllithium in hexane (0.95 mL, 2.4 mmol). The reaction was stirred for 2 h at −78° C. N,N-dimethylformamide (292 mg, 4 mmol) was added and the reaction continued to stir at −78° C. for 1 h, then at room temperature for 2 h. The reaction was quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organics were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 1-(4-methoxyphenyl)-1H-pyrazole-4-carbaldehyde (80 mg, 20%) as a yellow oil. 1H NMR (400 MHz, CDCl3, δ): 9.95 (s, 1H), 8.33 (s, 1H), 8.13 (s, 1H), 7.62 (d, J=9.2 Hz, 2H), 7.01 (d, J=9.2 Hz, 2H), 3.86 (s, 3H).

1. stirringto stir at −78° C. for 1 h
2. waitat room temperature for 2 h
3. customThe reaction was quenched with saturated ammonium chloride (20 mL)
4. extractionextracted with ethyl acetate (3×30 mL)
5. washThe combined organics were washed with brine (30 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by column chromatography

ORD record

ord-b7238376372146d7ad64c952659f171a

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859591B2