Morpholine → HCID 59526240, compound

HRID 385900Notes

Reaction equation

HRID 385900 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[N:8]=1)[C:3]([O:5][CH3:6])=[O:4].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:13][C:9]1[N:8]=[C:7]([CH:2]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:3]([O:5][CH3:6])=[O:4])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 59526058HCID 59526058, compound

Product 1

HCID 59526240HCID 59526240, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl bromo(6-bromopyridin-2-yl)acetate (1.00 g, 3.24 mmol) was taken up in DMF (10 mL) and morpholine (367 μL, 4.21 mmol) and DIEA (848 μL, 4.86 mmol) were added. After maintaining the reaction at room temperature overnight, the reaction was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. Silica gel chromatography (0-100% EtOAc/hexanes) afforded the title compound as a yellow oil.

Workup

  1. temperatureAfter maintaining
  2. customthe reaction at room temperature overnight
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eba65bc3749e4301802fa462fd726936
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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