6-Chloroindole → HCID 24823777, compound

HRID 2353510Notes

Reaction equation

HRID 2353510 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([Mg]Br)C.[CH3:15][C:16]1([CH3:24])[C:18]([CH3:20])([CH3:19])[CH:17]1[C:21](Cl)=[O:22]>ClCCl.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:21]([CH:17]3[C:18]([CH3:20])([CH3:19])[C:16]3([CH3:24])[CH3:15])=[O:22])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 871116-ChloroindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823777HCID 24823777, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-chloroindole (0.38 g, 2.5 mmol), ethylmagnesium bromide (1.0 M solution in THF, 3.0 mL, 3.0 mmol), zinc chloride (1.0 M solution in Et2O, 3.0 mL, 3.0 mmol) and the product of Example 1A (3.0 mmol) in 10 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.23 g, 0.83 mmol, 34% yield). MS (DCI/NH3) m/z 276 (M+H)+.

Sources & evidence

ORD record
ord-fdc9f4a03eee440799ba9ff8f532e455
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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