2-but-3-ynyl-2H-benzo[d][1,2,3]triazole → 2-(4-(pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 334619Notes

Reaction equation

HRID 334619 reaction equation
[CH2:1]([N:5]1[N:9]=[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]2=[N:6]1)[CH2:2][C:3]#[CH:4].C([N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26]C=2N=N1)CC#C>>[N:18]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[C:4]#[C:3][CH2:2][CH2:1][N:5]1[N:6]=[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]2=[N:9]1

Participants

3

Reactant 2

HCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazoleHCID 860867341-(but-3-ynyl)-1H-benzo[d][1,2,3]triazole

Product 1

HCID 665982202-(4-(pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 8%

Procedure

The title compounds were prepared in accordance with the general method of Example 108(C), from 90 mg (0.53 mmol) of 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole and 1-(but-3-ynyl)-1H-benzo[d][1,2,3]triazole. The crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2) to yield 10 mg (42 μmol, 8%) of 2-(4-(pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as an orange oil with a purity of 82%. Another fraction yielded after SCX column (DCM, DCM/MeOH 98:2, DCM/MeOH/NH4OH 95:4:1 to 94:4:2) 19 mg (76 μmol, 14%) of 1-(4-(pyridin-2-yl)but-3-ynyl)-1H-benzo[d][1,2,3]triazole as an orange oil.

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2)

Sources & evidence

ORD record
ord-b4650cfd0684431d87f0117084b03053
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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