ChemicalBook > CAS DataBase List > (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-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

Product Name
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
CAS No.
886230-77-9
Chemical Name
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Synonyms
(E)-6-iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole;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-...;(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;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-Iodo-3-[2-(pyridin-2-yl)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
CBNumber
CB32500682
Molecular Formula
C19H18IN3O
Formula Weight
431.27
MOL File
886230-77-9.mol
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(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole Property

Melting point:
156-159°C
Boiling point:
561.2±50.0 °C(Predicted)
Density 
1.60
storage temp. 
2-8°C(protect from light)
solubility 
Chloroform, DMSO, Methanol
pka
4.25±0.10(Predicted)
form 
Solid
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
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

AK Scientific
Product number
0034AP
Product name
(E)-6-iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Packaging
10g
Price
$497
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
HCH0045046
Product name
(E)-6-IODO-3-(2-(PYRIDIN-2-YL)VINYL)-1-(TETRAHYDRO-2H-PYRAN-2-YL)-1H-INDAZOLE
Purity
95.00%
Packaging
5MG
Price
$504.14
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
59207
Product name
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Packaging
2.5g
Price
$2120
Updated
2021/12/16
Ambeed
Product number
A143415
Product name
(E)-6-Iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Purity
98%
Packaging
250mg
Price
$26
Updated
2021/12/16
Ambeed
Product number
A143415
Product name
(E)-6-Iodo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Purity
98%
Packaging
1g
Price
$65
Updated
2021/12/16
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(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole Chemical Properties,Usage,Production

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) . Axitinib is used in cancer therapy. Axitinib (AG-013736) is a selective small molecule inhibitor of VEGF receptor tyrosine kinases 1, 2 and 3 and the platelet-derived growth factor (PDGF) receptor that targets the catalytic domain of the tyrosine kinase and induces ATP-competitive inhibition with limited activity against other protein kinases . It is an indazole derivative, its molecular formula is C22H18N4OS and its molecular weight is 386.5 Da[1].

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.

(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole Preparation Products And Raw materials

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View Lastest Price from (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole manufacturers

Zison Pharmaceutical (Shandong) Co., Ltd.
Product
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 886230-77-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98% by HPLC
Supply Ability
50kg/month
Release date
2023-01-05
Jinan Ande Pharmaceutical Co.,Ltd.
Product
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 886230-77-9
Price
US $0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100
Release date
2021-12-23
Career Henan Chemical Co
Product
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 886230-77-9
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200kgs
Release date
2020-03-05

886230-77-9, (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleRelated Search:


  • (E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
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  • (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)vinyl)-1-(tetrahydro-2H-pyran-2-yl)
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  • 1H-Indazole, 6-iodo-3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-
  • (E)-6-LODO-3-{2-(PYRIDIN-2-YL)ETHENYL}-1-(TETRAHYDRO-2H-PYRAN-2-YL)-1H-INDAZOLE
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  • 6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
  • 886230-77-9
  • Intermediate of Axitinib
  • intermediate