Sodium hydride → HCID 68463703, compound

HRID 506667Notes

Reaction equation

HRID 506667 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-4f98c17f7d624bd39710bf4c1d437124
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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