Sodium hydride → HCID 68578275, compound

HRID 642676Notes

Reaction equation

HRID 642676 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+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[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

4

Reactant 2

HCID 24758Sodium hydrideHCID 68577977HCID 68577977, compound

Product 1

HCID 68578275HCID 68578275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester (50 mg, from Exp. 64.2.) in dimethylformamide (1.5 ml) was added NaH (1.3 eq.), the mixture was stirred at 22° C. for 30 min. and cooled to 0° C. Ethylbromo acetate (33 mg) was added, the mixture was stirred for 2 h and partitioned between aqueous NH4Cl and AcOEt. The organic layer was dried, evaporated and the residue was chromatographed on silica (n-heptane/AcOEt, 10:1) to give 1-ethoxycarbonylmethyl-3-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid ethyl ester which was hydrolyzed as described in the general procedure B (Exp. 2.2) to give the title compound as a white solid. MS: 358.2 ([M−H]−).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture was stirred for 2 h
  3. custompartitioned between aqueous NH4Cl and AcOEt
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica (n-heptane/AcOEt, 10:1)

Sources & evidence

ORD record
ord-40a429e202114c12b405f6fa51f7055b
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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