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

HRID 334655Notes

Reaction equation

HRID 334655 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:10])[F:9])[N:3]=1.[CH2:11]([N:15]1[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]2=[N:16]1)[CH2:12][C:13]#[CH:14]>>[F:9][CH:8]([F:10])[C:4]1[N:3]=[C:2]([C:14]#[C:13][CH2:12][CH2:11][N:15]2[N:16]=[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]3=[N:19]2)[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 101044892-Bromo-6-(difluoromethyl)pyridineHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665981682-(4-(6-(difluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazoleYield 8.4%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(difluoromethyl)-pyridine (121 mg, 0.58 mmol) and 2-(but-3-ynyl)-2H-benzo[d][1,2,3]triazole (100 mg, 0.58 mmol, Example 109(D)). Reaction time: 2 hours. The crude residue was purified by preparative chromatography plate (DCM/MeOH 99:1) to yield 15 mg (49 μmol, 8%) of 2-(4-(6-(difluoromethyl)pyridin-2-yl)but-3-ynyl)-2H-benzo[d][1,2,3]triazole as a white solid (M.P.: 101.8-102.9° C.).

Workup

  1. customReaction time
  2. custom2 hours
  3. customThe crude residue was purified by preparative chromatography plate (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-b16bf71920d84d95aab169164073b984
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

Loading…