2-Bromopyridine → 5-Methyl-2-[4-(2-pyridinyl)-3-butyn-1-yl]-2H-benzotriazole

HRID 1189216Notes

Reaction equation

HRID 1189216 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([N:12]1[N:16]=[C:15]2[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:14]2=[N:13]1)[CH2:9][C:10]#[CH:11]>>[CH3:21][C:19]1[CH:18]=[CH:17][C:15]2=[N:16][N:12]([CH2:8][CH2:9][C:10]#[C:11][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[N:13]=[C:14]2[CH:20]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 86086760HCID 86086760, compound

Product 1

HCID 665981985-Methyl-2-[4-(2-pyridinyl)-3-butyn-1-yl]-2H-benzotriazoleYield 37%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (66 mg, 0.42 mmol) and 2-but-3-ynyl-5-methyl-2H-benzo[d][1,2,3]triazole (70 mg, 0.38 mmol, Example 165(B)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 36 mg (0.14 mmol, 37%) of 5-methyl-2-(4-(pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as an orange solid.

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-38c89c677eca4597a045419991358ee8
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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