1H-Benzotriazole → 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole

HRID 422375Notes

Reaction equation

HRID 422375 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[N:10]1[NH:11][N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12>>[F:9][CH2:8][C:4]1[N:3]=[C:2]([C:8]#[C:4][CH2:5][CH2:6][N:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3=[N:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 72201H-BenzotriazoleHCID 102416102-Bromo-6-(fluoromethyl)pyridine

Product 1

HCID 665977552-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 75.9%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(fluoromethyl)-pyridine (111 mg, 0.58 mmol, Example 190(E)) and 2-but-3-ynyl)-2H-benzo[d][1,2,3]triazole (100 mg, 0.58 mmol, Example 109(D)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 61 mg (0.22 mmol, 37%) of 2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a grey 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-2cfbd714acde42abb4651da4f019c590
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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