Sodium hydride → 4-[2,3,5-Trifluoro-6-(2-morpholin-4-yl-ethoxy)-pyridin-4-yl]-morpholine

HRID 1920883Notes

Reaction equation

HRID 1920883 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([F:15])=[C:4]([F:16])[N:3]=1.[OH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[H-].[Na+]>O1CCCC1>[F:16][C:4]1[C:5]([F:15])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:7]([F:8])=[C:2]([O:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 674918494-(2,3,5,6-Tetrafluoro-pyridin-4-yl)-morpholine

Product 1

HCID 674915344-[2,3,5-Trifluoro-6-(2-morpholin-4-yl-ethoxy)-pyridin-4-yl]-morpholineYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2,3,5,6-Tetrafluoro-pyridin-4-yl)-morpholine (2.36 g; 10 mmol) was dissolved in tetrahydrofuran (50 mL). To the solution was added 4-(2-hydroxyethyl)-morpholine (1.57 g; 12 mmol) followed by sodium hydride (288 mg; 12 mmol), and it was stirred overnight. The solvent was then evaporated, and the solid was purified by column chromatography to give 4-[2,3,5-trifluoro-6-(2-morpholin-4-yl-ethoxy)-pyridin-4-yl]-morpholine (3.3 g).

Workup

  1. customThe solvent was then evaporated
  2. customthe solid was purified by column chromatography

Sources & evidence

ORD record
ord-bc54f641dabf47f191b274a17d7c63e6
Source dataset
uspto-grants-2012_05
Patent number
US08173651B2

Reaction notes

Loading…