Sodium Chloride → HCID 22131131, compound

HRID 44305Notes

Reaction equation

HRID 44305 reaction equation
[Li+].[Br-].[BH4-].[Na+].[O:5]=[C:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:15][C:16](OCC)=[O:17])[CH:12]=2)[NH:7]1.B(OC)(OC)OC.[Na+].[Cl-]>C1COCC1.OS(O)(=O)=O>[OH:17][CH2:16][CH2:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:5])[CH2:14]2

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8470Trimethyl borateHCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 82551120Ethyl (2-oxo-2,3-dihydro-1H-indol-5-yl)acetate

Product 1

HCID 22131131HCID 22131131, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiBr (1.03 g) is added to a solution of NaBH4 (0.45 g) in THF (15 ml). The reaction mixture is heated at reflux for 7 hours, and the compound obtained in Step B (1.3 g) is added, followed by B(OMe)3 (0.067 ml). After refluxing for 18 hours, the mixture is concentrated under reduced pressure and the residue obtained is taken up in 20 ml of 3N H2SO4. The aqueous phase is saturated with NaCl and extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and evaporated to dryness. The residue is purified on silica gel (SiO2, eluant: AcOEt) to yield the title product in the form of a beige solid. The compound obtained is used directly in the next reaction.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 7 hours
  3. temperatureAfter refluxing for 18 hours
  4. concentrationthe mixture is concentrated under reduced pressure
  5. customthe residue obtained
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue is purified on silica gel (SiO2, eluant: AcOEt)

Sources & evidence

ORD record
ord-5cacf02494ab456aa5d2a63bfab4ce5b
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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