Sodium hydride → HCID 90004979, compound

HRID 1771391Notes

Reaction equation

HRID 1771391 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][OH:11])[CH2:5][CH2:4]1.F[C:13]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][N:14]=1>C1COCC1.O>[I:19][C:16]1[CH:17]=[CH:18][C:13]([O:11][CH2:10][CH2:9][N:6]2[CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 27831792-Fluoro-5-iodopyridine

Product 1

HCID 90004979HCID 90004979, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium hydride (2.15 g, 60% dispersion in mineral oil, 54.0 mmol) in THF (100 mL) at 0° C. was added 2-morpholinoethanol (5.43 mL, 44.8 mL). After 30 min 2-fluoro-5-iodopyridine (10.0 g, 44.8 mmol) was added and the reaction mixture was heated to 60° C. for 16 hr and was then cooled and diluted with water (75 mL). The resulting mixture was extracted with EtOAc (2×75 mL) and the combined organic extracts were dried and evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, 120 g, 20-60% EtOAc in isohexane, gradient elution) to afford 4-(2-(5-iodopyridin-2-yloxy)ethyl)morpholine as a yellow oil (9.35 g, 60%); Rt 0.94 min (Method 2, acidic); m/z 335 (M+H)+, (ES+).

Workup

  1. temperaturewas then cooled
  2. extractionThe resulting mixture was extracted with EtOAc (2×75 mL)
  3. customthe combined organic extracts were dried
  4. customevaporated in vacuo
  5. customthe residue was purified by flash column chromatography (SiO2, 120 g, 20-60% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-17f3b48445f94b04950e516943225a85
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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