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

HRID 1189337Notes

Reaction equation

HRID 1189337 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]=[CH:20][N:19]=1>>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[CH:7]=[N:6][N:5]([CH2:1][CH2:2][C:3]#[C:4][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:9]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 860868762-(but-3-ynyl)-4-(4-fluorophenyl)-2H-1,2,3-triazole

Product 1

HCID 665984202-(4-(4-(4-fluorophenyl)-2H-1,2,3-triazol-2-yl)but-1-ynyl)pyridineYield 41.4%

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-bromopyridine (122 mg, 0.77 mmol). The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 84 mg (0.29 mmol, 41%) of 2-(4-(4-(4-fluorophenyl)-2H-1,2,3-triazol-2-yl)but-1-ynyl)pyridine as a yellow solid (M.P.=83.5-84.5° C.).

Workup

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

Sources & evidence

ORD record
ord-a4d0d3486a4b40c4a33774d6789d8ab1
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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