6-(Bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine → Ethyl 3-cyclopropyl-3-(2-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)pyridin-4-yl)propanoate

HRID 709757Notes

Reaction equation

HRID 709757 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:5][CH:4]=1.[CH:23]1([CH:26]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([OH:39])[CH:34]=2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:25][CH2:24]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH:23]1([CH:26]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH2:2][C:3]3[CH:4]=[CH:5][C:6]([C:14]4[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=4[F:22])=[C:7]([CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11])[N:8]=3)[CH:34]=2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 1177602646-(Bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridineHCID 178471092HCID 178471092, compound

Product 1

HCID 117760063Ethyl 3-cyclopropyl-3-(2-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)pyridin-4-yl)propanoateYield 76.7%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 6-(bromomethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine (200 mg) in toluene (3.0 mL) were added ethyl 3-cyclopropyl-3-(2-hydroxypyridin-4-yl)propanoate (141 mg) and silver carbonate (166 mg), and the mixture was heated under reflux for 3 hr. The reaction mixture was cooled to room temperature, and filtered. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (218 mg) as a pale-yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. filtrationfiltered
  4. customThe solvent in the filtrate was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-49e7c616b15b496e835f3b4db4410a52
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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