2-Bromopyridine → 1H-Benzotriazole

HRID 422388Notes

Reaction equation

HRID 422388 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][CH:19]=[C:20]([Cl:21])[C:14]2=[N:13]1)[CH2:9][C:10]#[CH:11]>>[Cl:21][C:20]1[C:14]2[C:15](=[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]=2)[CH:17]=[CH:18][CH:19]=1.[N:13]1[NH:12][N:16]=[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=12

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 860868812-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole

Product 2

HCID 72201H-BenzotriazoleHCID 665978994-Chloro-2-(4-(pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-pyridine (25 mg, 0.16 mmol) and 2-(but-3-ynyl)-4-chloro-2H-benzo[d][1,2,3]triazole (30 mg, 0.15 mmol). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 12 mg (42 μmol, 29%) of 4-chloro-2-(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-36be5b4b8954427f885db03102f358c5
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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