Sodium hydride → HCID 58213802, compound

HRID 1400670Notes

Reaction equation

HRID 1400670 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].CS(O[CH2:19][C:20]1[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)(=O)=O.[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:27][O:26][C:23]1[N:22]=[CH:21][C:20]([CH2:19][N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=3)[CH:9]=[CH:10]2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylateHCID 58213827HCID 58213827, compound

Product 1

HCID 58213802HCID 58213802, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-indole-6-carboxylic acid methyl ester (0.54 g, 3.1 mmol) and (6-methoxypyridin-3-yl)methyl methanesulfonate (0.73 g, 3.4 mmol) in DMF (15 mL) was added NaH (0.9 g, 3.7 mmol). After stirring at room temperature for 1 hr, the solution was diluted with ethyl acetate (100 ml) and washed with water (100 ml). The organic layer was dried (MgSO4), filtered and concentrated. The remaining residue was subjected to flash chromatography (40% ethyl acetate/hexane) to provide 0.68 g (75%) of methyl 1-((6-methoxypyridin-3-yl)methyl)-1H-indole-6-carboxylate as a colorless oil.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4881b6c9fcbc4f8f8a8682c356cd08a2
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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