1-Cyclopropyl-4-iodo-1H-pyrazole Chemical Properties

storage temp. 

2-8°C(protect from light)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C6H7IN2/c7-5-3-8-9(4-5)6-1-2-6/h3-4,6H,1-2H2

InChIKey

JBWOMLVMUQFTFQ-UHFFFAOYSA-N

SMILES

N1(C2CC2)C=C(I)C=N1

1-Cyclopropyl-4-iodo-1H-pyrazole Usage And Synthesis

Uses

1-Cyclopropyl-4-iodo-1H-pyrazole is a useful chemical for the preparation of dihydropyridinone MGAT2 inhibitor.

Synthesis

Synthesis of 1-cyclopropyl-4-iodo-1H-pyrazole: 4-iodo-1H-pyrazole (645 mg, 3.33 mmol), cyclopropylboronic acid (571 mg, 6.65 mmol), copper(II) acetate (604 mg, 3.33 mmol), and DMAP (1219 mg, 9.98 mmol) were dissolved in dioxane (10 mL) and added with 0.323 mL (3.99 mmol) of pyridine. The reaction mixture was heated to 100 °C in air for 16 hours. After completion of the reaction, the mixture was concentrated in vacuum and diluted with EtOAc. The organic layer was washed with 1 M HCl and subsequently dried with MgSO4, filtered and concentrated in vacuum. The crude product was purified by column chromatography to afford Intermediate 10A (660 mg, 2.82 mmol, 85% yield) as a light yellow liquid.LCMS analysis: calculated value for C6H7N2 was 234.04 and measured value [M + H] was 234.9.

References

[1] Patent: WO2015/134701, 2015, A1. Location in patent: Page/Page column 58
[2] Patent: US2011/230462, 2011, A1. Location in patent: Page/Page column 84

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