(5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol → HCID 117760191, compound

HRID 709825Notes

Reaction equation

HRID 709825 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[F:20].[CH:23]1([CH:26]([C:33]2[C:38]([F:39])=[CH:37][N:36]=[C:35](O)[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.[Ag]=O>[CH:23]1([CH:26]([C:33]2[C:38]([F:39])=[CH:37][N:36]=[C:35]([O:11][CH2:10][C:8]3[CH:7]=[CH:6][C:5]([C:12]4[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=4[F:20])=[C:4]([CH2:3][C:2]([CH3:22])([CH3:21])[CH3:1])[N:9]=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 117759814(5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanolHCID 178471099HCID 178471099, compound

Product 1

HCID 117760191HCID 117760191, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Procedure

Silver oxide (327 mg) was added to a solution of (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (415 mg) and ethyl 3-cyclopropyl-3-(5-fluoro-2-hydroxypyridin-4-yl)propanoate (300 mg) in toluene (5 mL) at room temperature, and the mixture was heated under reflux for 2 hr. The reaction mixture was filtered, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (379 mg) as a pale-yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. filtrationThe reaction mixture was filtered
  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-b9292c1744f9449c80896aa9226c0998
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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