Sodium hydride → HCID 68579531, compound

HRID 642677Notes

Reaction equation

HRID 642677 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+].Br[CH2:29][CH2:30][O:31][CH3:32]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:29][CH2:30][O:31][CH3:32])[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

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 68577977HCID 68577977, compound

Product 1

HCID 68579531HCID 68579531, 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 (170 mg, from Exp. 64.2.) in dimethylformamide (1.0 ml) was added NaH (1.3 eq.), the mixture was stirred at 22° C. for 30 min. 1-Bromo-2-methoxy-ethane (99 mg) was added, the mixture was stirred for 17 h and partitioned between aqueous NH4Cl and AcOEt. The organic layer was dried, evaporated and the residue was chromatographed on silica (n-heptane/AcOEt, 20:1) to give 1-(2-methoxy-ethyl)-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 semisolid. MS: 358.1 ([M−H]−).

Workup

  1. stirringthe mixture was stirred for 17 h
  2. custompartitioned between aqueous NH4Cl and AcOEt
  3. customThe organic layer was dried
  4. customevaporated
  5. customthe residue was chromatographed on silica (n-heptane/AcOEt, 20:1)

Sources & evidence

ORD record
ord-21ac020b39444f8cb1ebe85b4e9cf613
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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