1H-indole-6-carbonitrile → 3-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrile

HRID 2353528Notes

Reaction equation

HRID 2353528 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1)#[N:2].C([Mg]Br)C.[CH3:16][C:17]1([CH3:25])[C:19]([CH3:21])([CH3:20])[CH:18]1[C:22](Cl)=[O:23]>[Cl-].[Zn+2].[Cl-]>[CH3:16][C:17]1([CH3:25])[C:19]([CH3:21])([CH3:20])[CH:18]1[C:22]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[NH:9][CH:8]=1)=[O:23]

Participants

5

Reactant 3

HCID 851461H-indole-6-carbonitrileHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 248244803-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carbonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 6-cyanoindole (Lancaster, 1.0 g, 7.0 mmol), ethylmagnesium bromide (1.0 M solution in THF, 8.4 mL, 8.4 mmol), zinc chloride (1.0 M solution in Et2O, 8.4 mL, 8.4 mmol) and the product of Example 1A (11 mmol) was processed as described in Example 1B to provide the title compound (0.91 g, 3.4 mmol, 49% yield). MS (DCI/NH3) m/z 267 (M+H)+.

Sources & evidence

ORD record
ord-28195e18f256477baa48fd4dde247f61
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

Loading…