Sodium hydride → HCID 58088458, compound

HRID 250208Notes

Reaction equation

HRID 250208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2.[H-].[Na+].[CH3:14][O:15][C:16](=[O:32])[C:17](=[CH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C>[CH3:14][O:15][C:16](=[O:32])[CH:17]([CH:25]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[O:2][CH3:1])[CH:8]=[CH:9]1)[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766607-Methoxy-1H-indoleHCID 67267624HCID 67267624, compound

Product 1

HCID 58088458HCID 58088458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-methoxyindole in DMF was added sodium hydride (0.086 g, 60% in oil) at 0° C. and the resulting mixture was stirred for 30 minutes. 2-Pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester (0.470 g) was added and the mixture was stirred for 2 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was washed twice with water and once with brine, then dried over magnesium sulfate, filtered and evaporated to dryness to afford the crude 2-[(7-methoxy-indol-1-yl)-pyridin-3-yl-methyl]-malonic acid tert-butyl ester methyl ester, which was crystallized from a hexane-ether mixture (0.207 g).

Workup

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic layer was washed twice with water and once with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f80701b00d3442db9f09c35f9d240327
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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