Sodium hydride → HCID 67114136, compound

HRID 1968868Notes

Reaction equation

HRID 1968868 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(OCC)=O)C.[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]2[CH2:28]O2)[N:21]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:15]([O:14][C:12]([C@@H:11]1[CH2:28][C@H:26]1[C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([F:19])[N:21]=1)=[O:13])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86761808HCID 86761808, compound

Product 1

HCID 67114136HCID 67114136, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (60% oil dispersion, 320 mg, 8 mmol) in toluene (10 mL) was added dropwise t-butyl diethylphosphonoacetate (1.92 g, 7.6 mmol). The resulting mixture was stirred at rt for 10 min., then a solution of 2-fluoro-6-oxiranyl-pyridine (530 mg, 3.8 mmol) in toluene (5 mL) was added dropwise to the reaction mixture. The resulting mixture was then heated at reflux for 12 h. The mixture was cooled to rt and diluted with EtOAc and washed with NH4Cl (saturated) and water. The EtOAc layer was dried (Na2SO4). The solvent was removed and the residue was subjected to ISCO (40 g column, hexane 3 min. then 0-60% EtOAc in hexane over 60 min.) to give the desired product (165 mg). MS (MH+ 238).

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureat reflux for 12 h
  3. temperatureThe mixture was cooled to rt
  4. washwashed with NH4Cl (saturated) and water
  5. dry with materialThe EtOAc layer was dried (Na2SO4)
  6. customThe solvent was removed
  7. custom40 g column, hexane 3 min.

Sources & evidence

ORD record
ord-9c31f9fc882c4a23a89a9224f765cd5e
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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