Dimethylformamide → 5-[1,3]Dioxolan-2-yl-2-(pyridin-2-yloxymethyl)-pyridine

HRID 78157Notes

Reaction equation

CN(C)C=O.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][OH:18])=[N:15][CH:16]=1.[H-].[Na+].F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>O>[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][O:18][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an N,N-dimethylformamide (40 mL) solution of (5-[1,3]dioxolan-2-yl-pyridin-2-yl)-methanol (1.37 g, 7.56 mmol) described in Manufacturing Example 154-1-4 was added sodium hydride (333 mg, 8.32 mmol, 60% in oil), which was stirred for 5 minutes at 0° C. Next, 2-fluoropyridine (716 μL, 8.32 mmol) was added to the reaction mixture, which was stirred for 45 minutes at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1 to 1:1) to obtain the title compound (1.51 g, 77%).

Workup

stirringwas stirred for 45 minutes at 50° C
extractionwhich was extracted with ethyl acetate
customThe organic layer was separated
washwashed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by silica gel column chromatography (heptane: ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record: ord-72aa5e07536d4e2cba59f67910645866
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Reaction notes

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