HCID 86603237, compound → HCID 66688380, compound

HRID 888075Notes

Reaction equation

HRID 888075 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([O:13][C:14]3[C:22]4[C:17](=[CH:18][C:19]([N+:23]([O-])=O)=[CH:20][CH:21]=4)[NH:16][N:15]=3)=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>[Pd]>[NH2:23][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([O:13][C:8]3[C:7]4[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=4)[NH:10][N:9]=3)=[N:15][NH:16]2)=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 86603237HCID 86603237, compound

Product 1

HCID 66688380HCID 66688380, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Indazolyl ethers can be prepared by the process outlined in Scheme 29. 6-Nitro-1H-2-hydroindazol-3-one 126 is protected such as with Boc2O and DMAP in CH2Cl2 at a temperature of about RT, to give the protected 6-nitro-2-hydroindazol-3-one. The protected 6-nitro-2-hydroindazol-3-one is reacted with an alcohol (where Rx is an appropriate substitutent selected from the possible substitutents on R) and Ph3P in a solvent, such as THF, and DEAD, at a temperature of about RT, to give the protected 6-nitro(indazol-3-yl)ether. The nitro intermediate is hydrogenated, such as with an H2 atmosphere in the presence of a catalyst, such as Pd/C, to give the protected 6-amino (indazol-3-yl)ether 127. The amine 127 is coupled and 2-chloronicotinic acid in a solvent, such as an alcohol, preferably pentanol, at a temperature above RT, preferably at a temperature above about 75° C., and more preferably at a temperature at about 130° C. to give the coupled and deprotected compound 128.

Sources & evidence

ORD record
ord-3a868bdd58264999845fa3179f789be8
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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