2-Bromo-6-(fluoromethyl)pyridine → HCID 66598197, compound

HRID 1189341Notes

Reaction equation

HRID 1189341 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1.[C:10]([O:14][C:15](=[O:31])[N:16]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30])[C:17](=[O:22])[CH2:18][CH2:19][C:20]#[CH:21])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([O:14][C:15](=[O:31])[N:16]([C:17](=[O:22])[CH2:18][CH2:19][C:20]#[C:21][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][F:9])[N:3]=1)[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH3:30])([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 102416102-Bromo-6-(fluoromethyl)pyridineHCID 86673179HCID 86673179, compound

Product 1

HCID 66598197HCID 66598197, compoundYield 79.7%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from 2-bromo-6-(fluoromethyl)pyridine (150 mg, 0.79 mmol, Example 190(E)) and (4-fluoro-2-methyl-phenyl)-pent-4-ynoyl-carbamic acid tert-butyl ester (241 mg, 0.79 mmol, 188(B)). Reaction time: 3 hours. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 260 mg (0.63 mmol, 79%) of [5-(6-fluoromethyl-pyridin-2-yl)-pent-4-ynoyl]-(4-fluoro-2-methyl-phenyl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1)

Sources & evidence

ORD record
ord-6b24307a2e9c48ff80222ce840120298
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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