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

HRID 709812Notes

Reaction equation

HRID 709812 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[F:17])=[N:7][CH:8]=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>C(=O)([O-])[O-].[Ag+2].C1(C)C=CC=CC=1>[CH:23]1([CH:26]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([O:39][CH2:2][C:3]3[CH:8]=[N:7][C:6]([C:9]4[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=4[F:17])=[C:5]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:4]=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 1177596225-(Bromomethyl)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridineHCID 178471092HCID 178471092, compound

Product 1

HCID 117760175Ethyl 3-cyclopropyl-3-(2-((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methoxy)pyridin-4-yl)propanoateYield 22.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-(bromomethyl)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine (88 mg), ethyl 3-cyclopropyl-3-(2-hydroxypyridin-4-yl)propanoate (62 mg), silver carbonate (72.6 mg) and toluene (2.0 mL) 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 (28 mg) as an orange oil.

Workup

  1. temperaturewas 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-3db89af0847a44c8afc0088aefab84c3
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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