Sodium Carbonate → HCID 86668063, compound

HRID 474091Notes

Reaction equation

HRID 474091 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16]O)[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[C:5]([Cl:8])=[N:6][CH:7]=1.CCN(S(F)(F)[F:24])CC.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][F:24])[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 86668062HCID 86668062, compound

Product 1

HCID 86668063HCID 86668063, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 5-(5-bromo-2-chloro-pyridin-3-yl)-5-hydroxymethyl-morpholin-3-one (547 mg, 1.70 mmol) in THF (13.6 ml) was added at 0° C. within 5 min a solution of DAST (1.01 ml, 7.65 mmol) in THF (7.2 ml), the reaction mixture was stirred at room temperature for 6 h. The mixture was cooled to 0° C., halfsaturated aq. Na2CO3 was added and the mixture was extracted with EtOAc, the combined organic layers were washed with halfsaturated aq. NaCl, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4) to provide the title compound as colorless solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with halfsaturated aq. NaCl
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4)

Sources & evidence

ORD record
ord-ddabb676c46b40fb89f008a7953862b4
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

Loading…