Sodium hydride → HCID 68463703, compound

HRID 2105352Notes

Reaction equation

HRID 2105352 reaction equation
C(O[C:4]([C:6]1[N:7]([CH2:23][CH2:24][CH2:25][NH2:26])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:10][CH:9]=2)=[O:5])C.[H-].[Na+]>CN(C)C=O.O.ClCCl>[CH2:16]([O:15][C:11]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:23][CH2:24][CH2:25][NH:26][C:4](=[O:5])[C:6]3=[CH:14][C:13]=2[CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 68460959HCID 68460959, compound

Product 1

HCID 68463703HCID 68463703, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 0.6 g (1.70 mmol) 1-(3-amino-propyl)-5-benzyloxy-1H-indole-2-carboxylic acid ethyl ester in 6 mL N,N-dimethylformamide, 85 μg (1.95 mmol; 55% dispersion in mineral oil) sodium hydride was added. After 2 hours the reaction mixture was diluted with water and dichloromethane, the phases were separated and the aqueous phase was washed three times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) to give the desired compound as a light yellow solid (67%).

Workup

  1. customthe phases were separated
  2. washthe aqueous phase was washed three times with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v)

Sources & evidence

ORD record
ord-0b1b36ae3d6b4df8b92abb8540a511e6
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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