Ethyl bromoacetate → Ethyl[(6-chloro-2-methylpyridin-3-yl)methoxy]acetate

HRID 385977Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([CH2:11][OH:12])=[CH:6][CH:5]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1.O>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:12][CH2:11][C:7]1[C:8]([CH3:10])=[N:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (266 mg of 60%, 6.66 mol) was suspended in tetrahydrofuran (14.8 mL) and cooled to 0° C. (6-Chloro-2-methylpyridin-3-yl)methanol (Example 421 Step 1) (350 mg, 2.22 mmol) was added and the mixture was stirred for 30 minutes at 0° C. Ethyl bromoacetate (0.25 mL, 2.22 mmol) was added and the solution was heated to 50° C. for 4 hours. The reaction mixture was then cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The aqueous layer was acidified with 1N HCl and extracted with ethyl acetate three times. All the organic layers were combined, dried over magnesium sulfate, filtered, concentrated, and purified via silica gel chromatography (0-100% ethyl acetate in hexane) to afford the title compound.

Workup

additionwas added
temperaturethe solution was heated to 50° C. for 4 hours
temperatureThe reaction mixture was then cooled to ambient temperature
extractionextracted with ethyl acetate
extractionextracted with ethyl acetate three times
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
custompurified via silica gel chromatography (0-100% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-9c0915778b7f4cab9abab802d34860c8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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