Sodium hydride → HCID 58092712, compound

HRID 1807699Notes

Reaction equation

HRID 1807699 reaction equation
[H-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH3:17])=[CH:10][N:9]=1)([OH:7])[CH3:6].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([O-])(O)=O.[Na+]>C1COCC1.O>[F:19][C:4]([F:3])([F:18])[C:5]([O:7][S:21]([CH3:20])(=[O:23])=[O:22])([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH3:17])=[CH:10][N:9]=1)[CH3:6]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 58092710HCID 58092710, compound

Product 1

HCID 58092712HCID 58092712, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 0.213 g (8.44 mmol) sodium hydride in 6 ml dry THF, 1.06 g (4.22 mmol) 1,1,1-trifluoro-2-(5-methoxymethoxy-pyridin-2-yl)-propan-2-ol (dissolved in 4.9 ml dry THF) was added dropwise at 0° C. After completion of the addition, stirring was continued for 3 h at room temperature. Then methanesulfonyl chloride (dissolved in 7.3 ml dry THF) was added at room temperature and stirring was continued for another 2 h. Then water and sat. NaHCO3 soln. were added. This mixture was extracted 2 times with EtOAc. The combinded organic layers were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 1.7 g of the title compound, which was used directly in the next step. LCMS (method L): tR=0.96 min, M+H=330.

Workup

  1. additionwas added dropwise at 0° C
  2. additionAfter completion of the addition
  3. stirringstirring
  4. waitwas continued for another 2 h
  5. additionwere added
  6. extractionThis mixture was extracted 2 times with EtOAc
  7. washThe combinded organic layers were washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86c2694e6a0a47e186b91181a7db9251
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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