2-(5-Bromopent-1-ynyl)pyridine → 1-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d][1,2,3]triazole

HRID 334635Notes

Reaction equation

HRID 334635 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1>>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]#[C:5][CH2:4][CH2:3][CH2:2][N:14]1[N:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]2=[N:13]1.[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]#[C:5][CH2:4][CH2:3][CH2:2][N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[N:14]1

Participants

4

Reactant 2

HCID 665979292-(5-Bromopent-1-ynyl)pyridineHCID 178418385HCID 178418385, compound

Product 2

HCID 665983111-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d][1,2,3]triazoleHCID 665985252-(5-(pyridin-2-yl)pent-4-ynyl)-2H-benzo[d][1,2,3]triazole

Procedure

The title compounds were prepared in accordance with the general method of Example 108(A), from 2-(5-bromo-pent-1-ynyl)-pyridine (298 mg, 0.66 mmol) and benzotriazole (72 mg, 0.60 mmol). The crude product was purified by flash chromatography (DCM/MeOH 99:1 to 98:2) to yield 2-(5-(pyridin-2-yl)pent-4-ynyl)-2H-benzo[d][1,2,3]triazole (27 mg, 0.1 mmol) as an orange oil and 1-(5-(pyridin-2-yl)pent-4-ynyl)-1H-benzo[d][1,2,3]triazole (27 mg, 0.1 mmol) as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-ad4a270655b445fa86959f6aa784b8e1
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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