Diisopropylethylamine → HCID 178513761, compound

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Reaction Steps

Scheme 2 illustrates the synthesis of compounds 9 and 10. Lithiation of compound 6 with n-BuLi followed by the addition of carbon dioxide affords 2-chloro-imidazole-4-carboxylic acid 7. Reaction of acid 7 with amine 2 in the presence of DMC and DIEA furnishes 2-chloro-imidazole-4-carboxamide 8, which undergoes Suzuki coupling reaction with arylboronic acid to give 2-aryl-imidazole-4-carboxamide 9. Reduction of amide 9 with Alane-N,N-dimethylethylamine complex gives compound 10. Alternatively, compound 10 is prepared from hydroxymethylimidazoles 12 via SOCl2 treatment and subsequent alkylation reaction with amine 2.

Provenance & Evidence