Water → Ethyl[2-(6-bromopyridin-2-yl)ethoxy]acetate
Reaction equation
[H-].[Na+].[Br:3][C:4]1[N:9]=[C:8]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:6][CH:5]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].O>O1CCCC1.C(OCC)(=O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:3])[N:9]=1)[CH3:19]Participants
Procedure
A solution of sodium hydride (74 mg, 1.87 mmol) in tetrahydrofuran (2 ml) was cooled to 0° C. 2-(6-Bromopyridin-2-yl)ethanol (Example 235, Step 3) (126 mg, 0.62 mmol) in tetrahydrofuran (2 ml) was added dropwise and the reaction was allowed to warm to room temperature. After 45 minutes at room temperature, the reaction was cooled to 0° C. and ethyl bromoacetate (0.14 ml, 1.25 mmol) was added. The reaction was allowed to warm to room temperature and then heated to 50° C. Upon completion, the reaction was cooled to 0° C. and water was added dropwise. Ethyl acetate was then added and the layers were separated. The organic layer was then dried over sodium sulfate, filtered and concentrated. Purification of the crude residue by silica gel chromatography afforded the title compound.
Workup
- temperaturethe reaction was cooled to 0° C.
- temperatureto warm to room temperature
- temperatureheated to 50° C
- temperatureUpon completion, the reaction was cooled to 0° C.
- customthe layers were separated
- dry with materialThe organic layer was then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification of the crude residue by silica gel chromatography
Sources & evidence
- ORD record
- ord-cc7b3c1ccd1449e389e5529d7e16899a
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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