Cesium carbonate → 3-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Acetoxymethyl Ester

HRID 1376128Notes

Reaction equation

HRID 1376128 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]([OH:19])=[O:18])=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:26]([O:29][CH2:30]Br)(=[O:28])[CH3:27]>CN(C=O)C>[C:26]([O:29][CH2:30][O:18][C:17]([C:9]1[NH:10][C:11]2[C:16]([C:8]=1[NH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:19])(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 101989283-(pyridin-4-ylamino)-1H-indole-2-carboxylic Acid

Product 1

HCID 103364213-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Acetoxymethyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Stir at 50° C. for 10 min. a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (1.27 g, 5 mmol) in DMF (25 mL), and add Cs2CO3 (1.63 g, 5 mmol). After 10 min. add bromomethyl acetate (0.95 g, 6.21 mmol) and one minute thereafter quench into aqueous NH4Cl solution. Extract with EtOAc and wash the extract with aqueous NaHCO3 solution. Dry the extract (MgSO4), filter and concentrate under vacuum to give a solid. Triturate the solid with EtOAc and obtain the title compound as a solid: MS 326(M+H).

Workup

  1. customthereafter quench into aqueous NH4Cl solution
  2. extractionExtract with EtOAc
  3. washwash the
  4. extractionextract with aqueous NaHCO3 solution
  5. customDry the
  6. extractionextract (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. customto give a solid
  10. customTriturate the solid with EtOAc

Sources & evidence

ORD record
ord-f80a60ee9c864a5b85fabf3988694099
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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