Water → 6-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine

HRID 70718

Reaction equation

[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][CH3:28])[N:21]=2)O)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].O>ClCCCl.[Pd](Cl)Cl>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([O:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:20]2[N:21]=[C:22]([O:27][CH3:28])[C:23]([Cl:26])=[CH:24][CH:25]=2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

Cyclopentylmethanol (0.039 mL) and palladium chloride (6.0 mg) were added to a solution of (4-tert-butylphenyl)(5-chloro-6-methoxypyridin-2-yl)methanol (110 mg) in 1,2-dichloroethane (2 mL) at room temperature, after which the mixture was stirred at 80° C. for six hours and then stirred at room temperature for two days. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 6-[(4-tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine as a pale red oil (112 mg, 86%).

Workup

stirringstirred at room temperature for two days
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customafter which the solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-7f44cb7813bb4de49faaf82451fc6b10
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Linked notes

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