Cesium carbonate → HCID 68950229, compound

HRID 2116730Notes

Reaction equation

HRID 2116730 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[C:16]([OH:21])[CH:15]=2)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32]>CC(C)=O.C(OCC)(=O)C>[CH2:34]([O:33][C:31](=[O:32])[CH:30]([O:21][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:12]([CH2:11][NH2:10])[NH:13]2)=[CH:18][CH:17]=1)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:35]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 84182Diethyl chloromalonateHCID 57605188HCID 57605188, compound

Product 1

HCID 68950229HCID 68950229, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(6-Hydroxy-1H-indol-2-ylmethyl)-carbamic acid benzyl ester was dissolved in 10 ml acetone, Cs2CO3 and diethyl chloromalonate were added. The reaction is stirred overnight. HPLC and TLC indicated the reaction is done. The mixture was diluted with ethyl acetate and filtered through silica gel plug. The filtrate is concentrated and redissolved in ethanol, hydrogenated for 3 hours at 40 psi of hydrogen. The mixture is filtered, washed with ethyl acetate. The filtrate is concentrated to give 2-(2-Aminomethyl-1H-indol-6-yloxy)-malonic acid diethyl ester.

Workup

  1. filtrationfiltered through silica gel plug
  2. concentrationThe filtrate is concentrated
  3. dissolutionredissolved in ethanol
  4. waithydrogenated for 3 hours at 40 psi of hydrogen
  5. filtrationThe mixture is filtered
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-c3f44ed520734320a9ab2a3921d28ce0
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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