6-Iodo-1H-indazole CAS 261953-36-0

Introduction：Basic information about 6-Iodo-1H-indazole CAS 261953-36-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

6-Iodo-1H-indazole Basic information

• Product Name: 6-Iodo-1H-indazole
• Synonyms: 6-IODO (1H)INDAZOLE;6-IODOINDAZOLE;6-iodo-1h1indazole;1H-Indazole, 6-iodo-;6-IodoindazoL;6-IODO (1H)INDAZOLE ISO 9001：2015 REACH;Axitinib Intermediate 3;6-Iodo-(1H)indazole, 96%
• CAS: 261953-36-0
• MF: C7H5IN2
• MW: 244.03
• EINECS: 607-884-2
• Product Categories: pharmacetical;Intermediate
• Mol File: 261953-36-0.mol

6-Iodo-1H-indazole Chemical Properties

• Melting point: 207.0 to 211.0 °C
• Boiling point: 358.2±15.0 °C(Predicted)
• density: 2.082±0.06 g/cm3(Predicted)
• storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• solubility: DMSO (Slightly), Methanol (Slightly)
• form: Liquid
• pka: 12.96±0.40(Predicted)
• color: Clear colorless to light yellow
• InChI: InChI=1S/C7H5IN2/c8-6-2-1-5-4-9-10-7(5)3-6/h1-4H,(H,9,10)
• InChIKey: RSGAXJZKQDNFEP-UHFFFAOYSA-N
• SMILES: N1C2=C(C=CC(I)=C2)C=N1

Safety Information

• HS Code: 29339980

6-Iodo-1H-indazole Usage And Synthesis

Physical Form

Light yellow to Brown powder to crystal

Uses

6-Iodo-1H-indazole is an intermediate used to synthesize inhibitors of Chk1.

Synthesis Reference(s)

[1] NOOLVI M N, PATEL H M. Small Molecule Tyrosine Kinase Inhibitors: The New Dawn for Cancer Therapy[J]. Letters in Drug Design & Discovery, 1900, 9(1): 84-125. DOI:10.2174/157018012798192892.

Synthesis

Revill P. and co-worker synthesized Axitinib by iodination of 6-iodo-1H-indazole (100) to give 3,6-di iodo-1H-indazole (101) ,which on further reaction with 2-mercapto-N-methylbenzenesulfinamide gives 2-(3-iodo-1Hindazol-6-ylthio)-N-methylbenzamide (101), the same can be obtained via 2-(1H-indazol-6-ylthion)-N-methylbenzamide (102) starting from 6-iodo-1H-indazole (100) through alternative route. N-protection of 2-(3-iodo-1H-indazol-6-ylthio)-N-methylbenzamide (101) by Boc2, DMAP or DHP, TsOH gives respective N-protected intermediates 103, 104. Further treatment of 103, 104 with 2-vinyl pyridine give rise to N-protected-2-(1-methyl-3-(2-(pyridine-2-yl) vinyl)-1Hindazole-6-ylthio) benzothioamide 105 and 106. Deprotection of 105 and 106 gives destination compound axitinib (107), the same can be obtained without protection from 2-(3-iodo-1H-indazol-6-ylthio)-N-methylbenzamide (101) by simple reaction with 2-vinyl pyridine^[1].

References

[1] Patent: EP3127900, 2017, A1. Location in patent: Paragraph 0250; 0251
[2] Patent: US6531491, 2003, B1
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Patent: US6716837, 2004, B1. Location in patent: Page column 30
[5] Patent: WO2017/68064, 2017, A1. Location in patent: Page/Page column 183; 184

6-Iodo-1H-indazole Preparation Products And Raw materials

• Raw materials: 1-(6-iodo-1H-indazol-1-yl)ethanone-->6-Aminoindazole-->6-Nitroindazole-->6-Bromoindazole-->Potassium iodide-->Hydrochloric acid-->Sodium nitrite-->5-IODO-2-METHYLANILINE
• Preparation Products: Axitinib Impurity B-->BenzaMide, 2-[(3-iodo-1H-indazol-6-yl)thio]-N-Methyl-