2-Bromo-6-(fluoromethyl)pyridine → HCID 66598305, compound

HRID 422407Notes

Reaction equation

HRID 422407 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[N:18]=[C:17]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:16]2=[N:15]1)[CH2:11][C:12]#[CH:13]>>[F:9][CH2:8][C:4]1[N:3]=[C:2]([C:8]#[C:4][CH2:5][CH2:6][C:22]2[C:16]3[C:17](=[N:18][NH:14][N:15]=3)[CH:19]=[CH:20][C:21]=2[CH3:23])[CH:7]=[CH:6][CH:5]=1.[F:9][CH2:8][C:4]1[N:3]=[C:2]([C:13]#[C:12][CH2:11][CH2:10][N:14]2[N:18]=[C:17]3[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:16]3=[N:15]2)[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 86086760HCID 86086760, compound

Product 2

HCID 66598305HCID 66598305, compoundYield 107.7%HCID 86630246HCID 86630246, compound

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(fluoromethyl)-pyridine (73 mg, 0.39 mmol) and 2-but-3-ynyl-5-methyl-2H-benzo[d][1,2,3]triazole (65 mg, 0.35 mmol). Reaction time: 3 hours. The crude residue was purified by flash chromatography (DCM/MeOH 99:1) to yield 40 mg (0.14 mmol, 39%) of 2-(4(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)-5-methyl-2H-benzo[d][1,2,3]triazole as a yellow solid.

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1)

Sources & evidence

ORD record
ord-999a89a0847845e4968ebdd27d37ba66
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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