Dimethylformamide → 2-(1-Cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyridine

HRID 1666544Notes

Reaction equation

[H-].[Na+].[CH:3]1([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C=O)C.F[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)=[CH:23][N:22]=1>O>[CH:3]1([N:8]2[CH2:9][CH2:10][CH:11]([O:14][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=4)=[CH:23][N:22]=3)[CH2:12][CH2:13]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 130 °C

Procedure

60% sodium hydride (13 mg) and 1-cyclopentyl-4-hydroxypiperidine (60 mg) were added to a DMF solution (3 ml) of 2-fluoro-5-[4-cyanophenyl]pyridine (56 mg), and stirred at 130° C. for 7 hours. The reaction mixture was cooled to room temperature, and water was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1) to obtain the entitled compound.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline solution
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified through silica gel column chromatography (C-300, chloroform:methanol=9:1)
customto obtain the entitled compound

Sources & evidence

ORD record: ord-f5e246c79d2a48bbab46721a125a7a27
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044070B2

Reaction notes

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