| Identification | Back Directory | [Name]
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole | [CAS]
886230-77-9 | [Synonyms]
6-iodo-1-(oxan-2-yl)-3-(2-pyridin-2-ylethenyl)indazole
(E)-6-iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)
6-Iodo-3-(2-pyridin-2-yl-vinyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole
6-iodo-3-((E)-2-(pyridin-2-yl-vinyl)
-1-(tetrahydropyran-2-yl)-1H-indazole
(E)-6-iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
6-Iodo-3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-Indazole
(E)-6-LODO-3-{2-(PYRIDIN-2-YL)ETHENYL}-1-(TETRAHYDRO-2H-PYRAN-2-YL)-1H-INDAZOLE
1H-Indazole, 6-iodo-3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-
(E)-6-iodo886230-77-9-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C19H18IN3O | [MDL Number]
MFCD12405576 | [MOL File]
886230-77-9.mol | [Molecular Weight]
431.27 |
| Chemical Properties | Back Directory | [Melting point ]
156-159°C | [Boiling point ]
561.2±50.0 °C(Predicted) | [density ]
1.60 | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Chloroform, DMSO, Methanol | [form ]
Solid | [pka]
4.25±0.10(Predicted) | [color ]
Light Yellow | [Stability:]
Hygroscopic, Light Sensitive | [InChI]
InChI=1S/C19H18IN3O/c20-14-7-9-16-17(10-8-15-5-1-3-11-21-15)22-23(18(16)13-14)19-6-2-4-12-24-19/h1,3,5,7-11,13,19H,2,4,6,12H2/b10-8+ | [InChIKey]
QXJFRDDGGSSQDX-CSKARUKUSA-N | [SMILES]
N1(C2OCCCC2)C2=C(C=CC(I)=C2)C(/C=C/C2=NC=CC=C2)=N1 |
| Hazard Information | Back Directory | [Uses]
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole is an intermediate used to prepare Axitinib (A794650) as a tyrosine kinase inhibitor. Axitinib is used in cancer therapy. | [Application]
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole is an intermediate used to prepare Axitinib (A794650) as a tyrosine kinase inhibitor. Axitinib is used in cancer therapy. | [Synthesis]
6-amino-3-((E)-2-pyridin-2-yl-vinyl)-1-(tetrahydropyran-2-yl)-1 H-indazole (100 g) dissolved in
acetic acid (6.5 L) is added over 1.5 hours to a solution of sodium nitrite (35 g) dissolved in
water (3.0 L) at 0℃ (-3 ± 3°C). The mixture is stirred for 1 hour at 0℃, and a solution of
hydrochloric acid (560 mL diluted in 1 L of water) at 0℃ is added over 15 minutes. The mixture
is stirred for 1 hour at 0℃. The formation of the diazonium salt is monitored by HPLC.
Dicholoromethane (400 ml) at O0C is added over 10 minutes to the diazonium salt solution at
0℃, and a solution of potassium iodide (207. 25 g) dissolved in water (300 ml) at O0C is added
over 1.5 hours. The reaction mixture is agitated for 3 hours at 0℃ (until complete by HPLC).
The mixture is then poured into a solution of sodium bisulfite in process water [Sodium bisulfite
(200g) dissolve in process water (500mL) at 27± 3°C] and Dicholoromethane (400 ml) below
270C, agitated, and the layers separated. The aqueous layer is extracted with Dichloromethane (100 ml) at 27℃ and combined. A solution of aqueous ammonia (100 ml) at 27± 3°C is added
over 40 minutes to the combined organic layers until the aqueous phase is basic (pH = 9 to 12).
Distill out dichloromethane and add methanol and heat to 50 ± 3°C and stir it at this temperature
for 15 min and then stir for 30 min at RT, followed by washing with methanol. Add
dichloromethane and heat to 45± 3°C and add activated carbon at this temperature. Followed by
addition of methanol and dichloromethane (if required) and stir the reaction mixture at 27± 3°C
for 30 min and cool it to 0±3°C and stir 1 hr and wash with methanol to provide (E)-6-Iodo-3-[2-
(pyridine-2yl)ethenyl]-1 -(tetrahydro-2H- pyran-2-yl)-1H-indazole. | [References]
[1] LESLIEISLA. Avelumab and axitinib in the treatment of renal cell carcinoma: safety and efficacy.[J]. Expert Review of Anticancer Therapy, 2020, 20 5: 343-354. DOI:10.1080/14737140.2020.1756780. |
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