| Identification | Back Directory | [Name]
6-IODO (1H)INDAZOLE | [CAS]
261953-36-0 | [Synonyms]
261953-36-0
6-IodoindazoL
6-IODOINDAZOLE
6-iodo-1h1indazole
6-IODO (1H)INDAZOLE
1H-Indazole, 6-iodo-
6-IODO (1H)INDAZOLE ISO 9001：2015 REACH | [EINECS(EC#)]
607-884-2 | [Molecular Formula]
C7H5IN2 | [MDL Number]
MFCD04114695 | [MOL File]
261953-36-0.mol | [Molecular Weight]
244.03 |
| Chemical Properties | Back Directory | [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. ]
Keep in dark place,Inert atmosphere,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 |
| Hazard Information | Back Directory | [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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