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)

pka

12.96±0.40(Predicted)

form 

Liquid

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].

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