6-Iodo-1H-indazole

Bezeichnung:6-Iodo-1H-indazole

CAS-Nr261953-36-0

Englisch Name:6-Iodo-1H-indazole

CBNumberCB2178484

SummenformelC7H5IN2

Molgewicht244.03

MOL-Datei261953-36-0.mol

6-Iodo-1H-indazole physikalisch-chemischer Eigenschaften

Schmelzpunkt	207.0 to 211.0 °C
Siedepunkt	358.2±15.0 °C(Predicted)
Dichte	2.082±0.06 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Liquid
pka	12.96±0.40(Predicted)
Farbe	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

Sicherheit

HS Code

29339980

Gefahreninformationscode (GHS)

6-Iodo-1H-indazole Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
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.
Synthese
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].
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

6-Iodo-1H-indazole Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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