Sodium hydride → HCID 68580361, compound

HRID 642735Notes

Reaction equation

HRID 642735 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].Cl[CH2:29][C:30]([N:32]([CH3:34])[CH3:33])=[O:31]>CN(C)C=O.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:29][C:30](=[O:31])[N:32]([CH3:34])[CH3:33])[C:8]2[C:13]([C:14]=1[CH2:15][C:16]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 68577977HCID 68577977, compound

Product 1

HCID 68580361HCID 68580361, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To as solution of 3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (46 mg, from Example 64.2.) in dimethylformamide (1 ml) was added 8 mg of NaH (55% in oil) and stirring was continued at 22° C. for 1 h. The mixture was treated with a solution of 2-chloro-N,N-dimethylacetamide (18 mg) in dimethylformamide (0.5 ml) and stirring was continued for 16 h. The mixture was diluted with saturated aqueous NaHCO3 and extracted with ethylacetate. The organic layer was washed with brine, dried, evaporated and the residue chromatographed on silica (n-heptane/AcOEt, 3:2) to give 1-dimethylcarbamoylmethyl-3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester as a colorless solid, MS: 415.4 ([M+H]+), which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give the title compound as a colorless solid. MS: 385.4 ([M−H]−).

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated
  7. customthe residue chromatographed on silica (n-heptane/AcOEt, 3:2)

Sources & evidence

ORD record
ord-74543dbc8da8435cbd94ff3d04221923
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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