Iodine → HCID 178506566, compound

HRID 2110263Notes

Reaction equation

HRID 2110263 reaction equation
[N+]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)([O-])=O.[I:13]I>>[I:13][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1

Participants

3

Reactant 2

HCID 807Iodine2×HCID 178526903HCID 178526903, compound

Product 1

HCID 178506566HCID 178506566, compound

Procedure

In step 1 of Scheme A, nitroindazole compound a is treated with iodine or iodine equivalent to form 3-iodo indazole compound b. The amine functionality at the 1-position may be protected (not shown) prior to carrying out this step, and then subsequently deprotected. In step 2 the iodoindazole b is reacted with aryl boronic acid c in the presence of suitable palladium catalyst to afford 3-aryl indazole d. Aryl boronic acid c may in certain embodiments be replaced with a corresponding heteroaryl boronic acid. In step 3 the nitro group on indazole compound d is reduced to yield amino-substituted indazole e. Indazole e in step 4 is then treated with arylsulfonyl chloride f to form the sulfonamide compound g, Compound g is a compound of formula Ia in accordance with the invention.

Sources & evidence

ORD record
ord-765a451d8b9141bba8606b829738ba36
Source dataset
uspto-grants-2009_04
Patent number
US07517901B2

Reaction notes

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