2-Bromo-6-(fluoromethyl)pyridine → 1H-Benzotriazole

HRID 334660Notes

Reaction equation

HRID 334660 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[CH2:10]([N:14]1[N:18]=[C:17]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:16]2=[N:15]1)[CH2:11][C:12]#[CH:13]>>[F:23][C:21]1[CH:20]=[CH:19][C:17]2=[N:18][N:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=3)[N:15]=[C:16]2[CH:22]=1.[N:15]1[NH:14][N:18]=[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=12

Participants

4

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860867982-(but-3-ynyl)-5-fluoro-2H-benzo[d][1,2,3]triazole

Product 2

HCID 72201H-BenzotriazoleHCID 665982075-Fluoro-2-(4-(6-(fluoromethyl)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-6-(fluoromethyl)-pyridine (55 mg, 0.29 mmol) and 2-(but-3-ynyl)-5-fluoro-2H-benzo[d][1,2,3]triazole (50 mg, 0.26 mmol). Reaction time: 13 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 50 mg (0.17 mmol, 64%) of 5-fluoro-2-(4-(6-fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a yellow solid.

Workup

  1. customReaction time
  2. custom13 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-b0a81c405bd9449db25ab1ff80ab5078
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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