1H-Indazole → 1H-Benzimidazole-2-carboxaldehyde

HRID 1869181Notes

Reaction equation

HRID 1869181 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)C=N1.C[N+:11]([CH3:14])=CCl.[Cl-].C(Cl)(=O)[C:17](Cl)=[O:18]>CN(C)C=O>[NH:11]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]=[C:14]1[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 92211H-IndazoleHCID 65578Oxalyl chlorideHCID 77311Chloro-N,N-dimethylformiminium chloride

Product 1

HCID 768261H-Benzimidazole-2-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In Step 1 of Scheme E, azaindole compound a is treated with the Vilsmeier reagent formed by mixing oxalyl chloride with dimethyl formamide to form azaindole aldehyde w, which in turn is reacted with Meldrum's acid in Step 2 to yield azaindole compound x. Azaindole x is then treated with Grignard reagent y in Step 3 to afford azaindole compound z. In Step 4 compound z is reacted with amine d in the presence of pyridine to give azaindole amide r, which is then reduced in Step 5 to provide aminopropyl azaindole compound s. Compound s is one of the compounds of formula I in accordance with the invention.

Workup

  1. customformed

Sources & evidence

ORD record
ord-7a3b4a23a1884e6da6e4ce6a91ee733b
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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