Aniline → HCID 66624089, compound

HRID 451370Notes

Reaction equation

HRID 451370 reaction equation
[NH2:1]C1C=CC=CC=1.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:11]=2[N:10]=[N:9]1>C(Cl)(Cl)Cl>[NH2:1][N:9]1[N:8]=[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:11]2=[N:10]1

Participants

4

Reactant 2

HCID 6115AnilineHCID 178420751HCID 178420751, compound

Product 1

HCID 66624089HCID 66624089, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Anilines of general formula 9m or the corresponding bromides 3m with an 2-propan-2-ol group in 5-position of the triazolopyridine (see Scheme 18) can be prepared starting from ester 51 by bromination in chloroform followed by cyclization as already described in Scheme 8 to give 2-amino-triazolopyridine 53. The ester 53 can then be treated with methyl magnesium bromide to provide the tertiary alcohol 54. Conversion of the bromide by e.g. Suzuki reaction gives aniline 9m or after Sandmeyer reaction bromide 3m. The starting material 51 is either commercially available or can be synthesized by methods known in the art, e.g for R=Me, 51 can be prepared from the corresponding bromide by reaction with trimethyl boroxine in the presence of a palladium catalyst.

Sources & evidence

ORD record
ord-3d1ed1494a4d440cb5cb8249de60ee9e
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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