2-Bromo-6-(fluoromethyl)pyridine → HCID 66597877, compound

HRID 334818Notes

Reaction equation

HRID 334818 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N: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[CH:9]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=3)[N:7]=[N:6]2)[N:19]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 86086799HCID 86086799, compound

Product 1

HCID 66597877HCID 66597877, compoundYield 21.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 1-(but-3-ynyl)-4-(4-fluorophenyl)-1H-1,2,3-triazole (100 mg, 0.47 mmol) and 2-bromo-6-(fluoromethyl)pyridine (97 mg, 0.51 mmol, Example 190(E)). Reaction time: 2 hours. The crude residue was purified by flash chromatography (DCM/MeOH 98.5:1.5) to yield 32 mg (0.10 mmol, 21%) of 2-(fluoromethyl)-6-(4-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)but-1-ynyl)pyridine as a yellow solid (M.P.=100-103° C.).

Workup

  1. customReaction time
  2. custom2 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 98.5:1.5)

Sources & evidence

ORD record
ord-1de25b00c7b44bda8de2ab21631ac5ca
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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