2-Bromo-6-(fluoromethyl)pyridine → 2-(fluoromethyl)-6-(4-(4-(4-fluorophenyl)-2H-1,2,3-triazol-2-yl)but-1-ynyl)pyridine

HRID 1189338Notes

Reaction equation

HRID 1189338 reaction equation
[CH2:1]([N:5]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=[N:6]1)[CH2:2][C:3]#[CH:4].Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][F:25])[N:19]=1>>[F:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:4]#[C:3][CH2:2][CH2:1][N:5]2[N:9]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)[CH:7]=[N:6]2)[N:19]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 860868762-(but-3-ynyl)-4-(4-fluorophenyl)-2H-1,2,3-triazole

Product 1

HCID 665978752-(fluoromethyl)-6-(4-(4-(4-fluorophenyl)-2H-1,2,3-triazol-2-yl)but-1-ynyl)pyridineYield 45%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-(but-3-ynyl)-4-(4-fluorophenyl)-2H-1,2,3-triazole (150 mg, 0.70 mmol, Example 254(B)) and 2-bromo-6-(fluoromethyl)pyridine (146 mg, 0.77 mmol, Example 190(E)). The crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5 to 99:1) to yield 101 mg (0.31 mmol, 45%) of 2-(fluoromethyl)-6-(4-(4-(4-fluorophenyl)-2H-1,2,3-triazol-2-yl)but-1-ynyl)pyridine as a yellow solid (M.P.=84-86° C.).

Workup

  1. customThe crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5 to 99:1)

Sources & evidence

ORD record
ord-79f364e3baf04340826e6693c04d50df
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

Loading…