Diethyl Ether → HCID 59255292, compound

HRID 1891705Notes

Reaction equation

[CH2:1]([O:3]CC)C.Br[C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[N:11][CH:12]=1.C([Li])CCC.CN(C)C=O>O>[F:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][C:10]1[N:11]=[CH:12][C:7]([CH:1]=[O:3])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a diethyl ether (100 mL) solution of 5-bromo-2-(3-fluorophenoxy)-pyridine (5.81 g, 21.7 mmol) described in Manufacturing Example 71-1-1 was added n-butyl lithium (13.8 mL, 1.57 M n-hexane solution, 21.7 mmol) under nitrogen atmosphere at −78° C., which was stirred for 40 minutes at −78° C. N,N-Dimethylformamide (2.02 mL, 26.0 mmol) was then added to the mixture at −78° C., and stirred for 25 minutes as the temperature was gradually raised to 0° C. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate. The organic layer was separated, washed with 1 N aqueous sodium hydroxide solution 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=5:1) to obtain the tile compound (2.47 g, 52%).

Workup

stirringstirred for 25 minutes as the temperature
temperaturewas gradually raised to 0° C
extractionwhich was then extracted with ethyl acetate
customThe organic layer was separated
washwashed with 1 N aqueous sodium hydroxide solution 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=5:1)

Sources & evidence

ORD record: ord-74a5cf38c622476c9fcfe8ad49b7ad8b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507530B2

Reaction notes

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