Sodium hydride → HCID 18794869, compound

HRID 1004210Notes

Reaction equation

HRID 1004210 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH2:13][C:14]#[N:15])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].[H-].[Na+]>CN(C=O)C>[CH3:16][C:17]([CH3:22])([CH3:21])[C:18]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[C:8]([CH2:13][C:14]#[N:15])=[CH:9]1)=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62493Pivaloyl chlorideHCID 2523851h-Indole-3-acetonitrile, 6-nitro-

Product 1

HCID 18794869HCID 18794869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure of Example 1, Step A, the N-alkylation reaction of 346.6 mg (1.72 mmol) of 6-nitro-1H-indolyl-3-acetonitrile (13) from Example 2, Step C with 0.3 ml (2.44 mmol) of trimethylacetyl chloride and 70.8 mg (1.77 mmol) of NaH (60% dispersion in oil) as a base in 8 ml of DMF yielded after chromatographic purification, 287.7 mg (43.2%) of [1-(2,2-dimethyl-propionyl)-6-nitro-1H-indol-3-yl]-acetonitrile (18) as a yellow oil.

Workup

  1. customyielded
  2. customafter chromatographic purification, 287.7 mg (43.2%) of [1-(2,2-dimethyl-propionyl)-6-nitro-1H-indol-3-yl]-acetonitrile (18) as a yellow oil

Sources & evidence

ORD record
ord-dc9a303db8354006b01491cc4857761a
Source dataset
uspto-grants-2000_04
Patent number
US06048887

Reaction notes

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