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

HRID 422389Notes

Reaction equation

HRID 422389 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][CH:21]=[C:22]([Cl:23])[C:16]2=[N:15]1)[CH2:11][C:12]#[CH:13]>>[Cl:23][C:22]1[C:16]2[C:17](=[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]=2)[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860868812-but-3-ynyl-4-chloro-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665983004-chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 35%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(fluoromethyl)-pyridine (30 mg, 0.16 mmol) and 2-(but-3-ynyl)-4-chloro-2H-benzo[d][1,2,3]triazole (30 mg, 0.15 mmol, Example 146(B)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 16-mg (51 μmol, 35%) of 4-chloro-2-(4-(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a brown oil.

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-85bd75e116644aa582de3a9ac8ceabe0
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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