4,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazole → 2-(pyrazin-2-yl)-2H-benzo[d][1,2,3]triazole

HRID 1050679Notes

Reaction equation

HRID 1050679 reaction equation
BrC1C2C(=NN(C3C=CN=CC=3)N=2)C(Br)=CC=1.Br[C:19]1[C:27]2[C:23](=[N:24][N:25]([C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[N:26]=2)[C:22](Br)=[CH:21][CH:20]=1>>[N:29]1[CH:30]=[CH:31][N:32]=[CH:33][C:28]=1[N:25]1[N:26]=[C:27]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]2=[N:24]1

Participants

3

Reactant 2

HCID 866799014,7-dibromo-2-(pyridin-4-yl)-2H-benzo[d][1,2,3]triazoleHCID 866799024,7-dibromo-2-(pyrazin-2-yl)-2H-benzo[d][1,2,3]triazole2×

Product 1

HCID 866799002-(pyrazin-2-yl)-2H-benzo[d][1,2,3]triazoleYield 23%

Procedure

A similar two-step procedure as that of Intermediate A was applied to give 2-(pyrazin-2-yl)-2H-benzo[d][1,2,3]triazole (23% yield) in the first step and 4,7-dibromo-2-(pyrazin-2-yl)-2H-benzo[d][1,2,3]triazole (Intermediate B, 26%) in the second step. 1H NMR (400 MHz, CDCl3): δ 9.75 (d, J=1.5 Hz, 1H, pyrazine), 8.81 (d, J=2.2 Hz, 1H, pyrazine), 8.71 (dd, J=2.5 and 1.5 Hz, 1H, pyrazine), 7.56 (s, 2H, benzotriazole).

Sources & evidence

ORD record
ord-24cabe92d46940f7abf22dda2f62be5f
Source dataset
uspto-grants-2016_07
Patent number
US09382424B2

Reaction notes

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