1,2-Dibromoethane → 1-(5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)-2-(3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)ethanol

HRID 1049530Notes

Reaction equation

HRID 1049530 reaction equation
BrCCBr.[Mg].[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15]1[CH:16]=[CH:17][C:18]([CH:26]=[O:27])=[N:19][C:20]=1[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23].Br[CH2:29][C:30]1[CH:31]=[C:32]([CH:41]=[CH:42][CH:43]=1)[CH2:33][O:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][O:36]1.[Cl-].[NH4+]>C1COCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15]1[CH:16]=[CH:17][C:18]([CH:26]([OH:27])[CH2:29][C:30]2[CH:43]=[CH:42][CH:41]=[C:32]([CH2:33][O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH:31]=2)=[N:19][C:20]=1[CH2:21][C:22]([CH3:24])([CH3:23])[CH3:25]

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 914805892-((3-(bromomethyl)benzyl)oxy)tetrahydro-2H-pyranHCID 1177598875-(2-Fluoro-5-methoxyphenyl)-6-neopentylpicolinealdehyde

Product 1

HCID 1177597051-(5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)-2-(3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)ethanolYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under a nitrogen atmosphere, 1,2-dibromoethane (34 μL) was added to a mixture of magnesium (578 mg) and THF (15 mL) at room temperature, and the mixture was stirred at 50° C. for 10 min. To the reaction mixture were added 5-(2-fluoro-5-methoxyphenyl)-6-neopentylpicolinealdehyde (2.39 g) and then 2-((3-(bromomethyl)benzyl)oxy)tetrahydro-2H-pyran (4.52 g) was added, and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (980 mg) as an orange oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39b4d455079644b1926ba8c1e0a12fee
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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