(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 Structure](CAS2/GIF/886230-77-9.gif)
- 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
- Molecular Weight:
- 431.27
- MOL File:
- 886230-77-9.mol
- Modify Date:
- 2023/11/6 13:01:33
| 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 |
(E)-6-Iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole Chemical Properties,Uses,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
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Molkem Chemicals | +91-917228022464 +91-7228022464 | Ahmedabad, India | 138 | 58 | Inquiry |
| Credas Labs Pvt Ltd | +91 9133918031 | Hyderabad, India | 119 | 58 | Inquiry |
| Rivashaa Agrotech Biopharma Pvt. Ltd. | +91-26463395 +91-7926462688 | Gujarat, India | 1615 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Zison Pharmaceutical (Shandong) Co., Ltd. | +86-0086-531-88259693 +86-18660188356 | China | 57 | 58 | Inquiry |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | China | 32835 | 60 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29899 | 58 | Inquiry |