2-Bromo-6-(fluoromethyl)pyridine → HCID 66598462, compound

HRID 334663Notes

Reaction equation

HRID 334663 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[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH:16]=[N:15]1)[CH2:11][C:12]#[CH:13]>>[F:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH:16]=[N:15]2)[N:3]=1

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 86086858HCID 86086858, compound

Product 1

HCID 66598462HCID 66598462, compoundYield 38.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(fluoromethyl)-pyridine (49 mg, 0.26 mmol) and 1-but-3-ynyl-4-(4-fluoro-phenyl)-1H-pyrazole (50 mg, 0.23 mmol, Example 140(A)). Reaction time: 13 hours. The crude residue was purified by flash chromatography (DCM/MeOH 98:2) to yield 29 mg (88 μmol, 38%) of 2-(fluoromethyl)-6-(4-(4-(4-fluorophenyl)-1H-pyrazol-1-yl)but-1-ynyl)pyridine as a yellow solid.

Workup

  1. customReaction time
  2. custom13 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 98:2)

Sources & evidence

ORD record
ord-348bd43470cc4546a9d22efb7bcaaa0b
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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