2-but-3-ynyl-2H-benzo[d][1,2,3]triazole → 1H-Benzotriazole

HRID 422343Notes

Reaction equation

HRID 422343 reaction equation
C([N:5]1[N:9]=[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]2=[N:6]1)CC#C.C(N1C2C=CC=CC=2N=N1)CC#C>>[N:6]1[NH:5][N:9]=[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=12

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 72201H-Benzotriazole

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 24-(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-9410b0aa83a84ed0b52295b067e5e526
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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