Cesium carbonate → HCID 68283247, compound

HRID 1527203Notes

Reaction equation

HRID 1527203 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[NH:7][CH:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]([O:25][CH2:26][CH2:27]Br)(=[O:24])[CH3:23]>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:27][CH2:26][O:25][C:22](=[O:24])[CH3:23])[CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 19372277HCID 19372277, compound

Product 1

HCID 68283247HCID 68283247, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (5-hydroxy-1H-indol-3-yl)-acetic acid methyl ester (670 mg, 3.26 mmol) in acetone (15 mL) was added cesium carbonate (1.17 g, 3.59 mmol) and 2-bromoethyl acetate (395 μL, 3.59 mmol). The suspension was refluxed overnight under nitrogen. Acetone was concentrated and the residue was dissolved in water and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 6:4) to give the desired material. TLC, Rf (c-hexane/EtOAc 1:1)=0.45; MS (LC-MS): 292.1 [M+H]+, 314.0 [M+Na]+, 290.0 [M−H]−; tR (HPLC conditions f): 1.70 min.

Workup

  1. temperatureThe suspension was refluxed overnight under nitrogen
  2. concentrationAcetone was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 6:4)

Sources & evidence

ORD record
ord-7af04b5efcf64858b63295d92995f1cb
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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