Potassium Carbonate → 3-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Diethylcarbamoyloxymethyl Ester

HRID 1376127Notes

Reaction equation

HRID 1376127 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.[CH2:20]([N:22]([CH2:28][CH3:29])[C:23](=[O:27])[O:24][CH2:25]Cl)[CH3:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:20]([N:22]([CH2:28][CH3:29])[C:23]([O:24][CH2:25][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:27])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 101989283-(pyridin-4-ylamino)-1H-indole-2-carboxylic AcidHCID 14800940Chloromethyl diethylcarbamate

Product 1

HCID 117406143-(Pyridin-4-ylamino)-1H-indole-2-carboxylic Acid Diethylcarbamoyloxymethyl EsterYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a mixture of 3-(4-pyridinylamino)-1H-indole-2-carboxylic acid (2.0 g, 8.0 mmol), chloromethyl diethylcarbamate (1.7 g, 10.4 mmol) and K2CO3 in DMF (50 mL) at ambient temperature overnight. Add EtOAc (400 mL), to the reaction mixture, wash the organic layer with brine solution (400 mL) and concentrate to an oil. Purify by flash chromatography over silica gel (40 g) eluting with EtOAc and then 10% MeOH/EtOAc. Collect like fractions and concentrate under vacuum to yield an oil. Crystallize from heptane-ether to obtain 1.1 g (36%) of the title compound as a white powder: MS 383(M+H).

Workup

  1. washAdd EtOAc (400 mL), to the reaction mixture, wash the organic layer with brine solution (400 mL)
  2. concentrationconcentrate to an oil
  3. customPurify by flash chromatography over silica gel (40 g)
  4. washeluting with EtOAc
  5. customCollect like fractions
  6. concentrationconcentrate under vacuum
  7. customto yield an oil
  8. customCrystallize from heptane-ether

Sources & evidence

ORD record
ord-3da80d6a3552443eb5391c6c35b5a321
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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