![](/CAS/GIF/66000-39-3.gif)
1-(4-CHLORO-PHENYL)-1H-PYRAZOL-3-YLAMINE synthesis
- Product Name:1-(4-CHLORO-PHENYL)-1H-PYRAZOL-3-YLAMINE
- CAS Number:66000-39-3
- Molecular formula:C9H8ClN3
- Molecular Weight:193.63
![3-Aminopyrazole](/CAS/GIF/1820-80-0.gif)
1820-80-0
465 suppliers
$5.00/5g
![1-Chloro-4-iodobenzene](/CAS/GIF/637-87-6.gif)
637-87-6
287 suppliers
$38.00/10 G
![1-(4-CHLORO-PHENYL)-1H-PYRAZOL-3-YLAMINE](/CAS/GIF/66000-39-3.gif)
66000-39-3
25 suppliers
$210.00/250mg
Yield: 57%
Reaction Conditions:
with caesium carbonate;copper(I) bromide in N,N-dimethyl-formamide at 120; for 14 h;Inert atmosphere;Sealed tube;
Steps:
1.1 1-(4-chlorophenyl)-1H-pyrazol-3-amine
[260] 1H-pyrazol-3-amine (500 mg, 6.02 mmol), 1-chloro-4-iodo-benzene (1.5 g, 6.29 mmol), copper (I) bromide (100 mg, 0.70 mmol), and cesium carbonate (3.0 g, 9.21 mmol) were combined and suspended in DMF (5.0 mL). The resultant mixture was heated in a sealed vessel at 120°C under an atmosphere of nitrogen for 14 h. The reaction mixture was partitioned into 1:1 ethyl acetate/water. The layers were separated, and the aqueous further extracted with ethyl acetate (2 x 20 mL). The combined organics were dried (Na2SO4), filtered, and concentrated. The crude residue was purified first by silica gel chromatography (40g column, linear gradient of 0-30% ethyl acetate in heptane; material obtained was a mixture of regioisomers), and second by C18 reverse phase chromatography (10- 50% acetonitrile/Water with TFA modifier). Pure fractions were washed with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered, and concentrated to provide 1-(4-chlorophenyl)-1H-pyrazol-3-amine (542 mg, 57% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.15 (d, J = 2.6 Hz, 1H), 7.79 - 7.58 (m, 2H), 7.52 - 7.27 (m, 2H), 5.75 (d, J = 2.6 Hz, 1H), 5.14 (s, 2H) ppm. ESI-MS m/z calc. 193.04, found 194.03 (M+1).
References:
VERTEX PHARMACEUTICALS INCORPORATED;CHARIFSON, Paul, S.;COME, Joh, H.;COURT, John, J.;GALE-DAY, Zachary;GU, Wenxin;JACKSON, Katrina, L.;MAGAVI, Sanjay, Shivayogi;NANTHAKUMAR, Suganthini, S.;RONKIN, Steven, Michael;SWETT, Rebecca, Jane;TANG, Qing WO2018/107056, 2018, A1 Location in patent:Paragraph 260
![1-(4-CHLORO-PHENYL)-4,5-DIHYDRO-1H-PYRAZOL-3-YLAMINE](/CAS/GIF/6508-11-8.gif)
6508-11-8
11 suppliers
inquiry
![1-(4-CHLORO-PHENYL)-1H-PYRAZOL-3-YLAMINE](/CAS/GIF/66000-39-3.gif)
66000-39-3
25 suppliers
$210.00/250mg
![3-Aminopyrazole](/CAS/GIF/1820-80-0.gif)
1820-80-0
465 suppliers
$5.00/5g
![1-Chloro-4-iodobenzene](/CAS/GIF/637-87-6.gif)
637-87-6
287 suppliers
$38.00/10 G
![1-(4-Chlorophenyl)-1H-pyrazol-5-amine](/CAS/20140602/GIF/CB72426917.gif)
14678-97-8
15 suppliers
$240.00/100mg
![1-(4-CHLORO-PHENYL)-1H-PYRAZOL-3-YLAMINE](/CAS/GIF/66000-39-3.gif)
66000-39-3
25 suppliers
$210.00/250mg