Indole-5-carbonitrile → HCID 24824479, compound

HRID 2353523Notes

Reaction equation

HRID 2353523 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[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]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:16][C:17]1([CH3:25])[C:19]([CH3:21])([CH3:20])[CH:18]1[C:22]([C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][CH:7]=1)=[O:23]

Participants

6

Reactant 3

HCID 27513Indole-5-carbonitrileHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824479HCID 24824479, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-cyanoindole (1.42 g, 10 mmol), ethylmagnesium bromide (1.0 M solution in THF, 11 mL, 11 mmol), zinc chloride (1.0 M solution in Et2O, 11 mL, 11 mmol) and the product of Example 1A (10 mmol) in 30 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.45 g, 1.7 mmol, 17% yield). MS (DCI/NH3) m/z 267 (M+H)+.

Sources & evidence

ORD record
ord-a81fcc2899cd465daae4e0668d647269
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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