Sodium hydride → HCID 15458809, compound

HRID 1004204Notes

Reaction equation

HRID 1004204 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.[CH3:13][C:14]([CH3:19])([CH3:18])[C:15](Cl)=[O:16].[H-].[Na+]>CN(C=O)C>[CH3:13][C:14]([CH3:19])([CH3:18])[C:15]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1)=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 351795Indole-3-acetonitrile

Product 1

HCID 15458809HCID 15458809, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure of subpart A above, the N-alkylation reaction of 10.2 g (65 mmol) of commercially available (1H-indol-3-yl)-acetonitrile (5) (1H-indol-3-yl)-acetonitrile (Acros Organics, Belgium) with 8.7 ml (71 mmol) of trimethylacetyl chloride and 3.4 g (85 mmol) of NaH (60% dispersion in oil) as a base in 115 ml of DMF yielded 6.6 g (38.7%) of [1-(2,2-dimethyl-propionyl)-1H-indol-3-yl]-acetonitrile (6) as a yellow oil after chromatographic purification.

Sources & evidence

ORD record
ord-83cf5257f24247ef981f9bf2d9900913
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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