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

HRID 640440Notes

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-5a19e8e7577745ae87b0565ac7eb0d23
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Reaction notes

Loading…