5-Chloroindole → HCID 24823776, compound

HRID 227433Notes

Reaction equation

HRID 227433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.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:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:21]([CH:17]1[C:18]([CH3:20])([CH3:19])[C:16]1([CH3:24])[CH3:15])=[O:22]

Participants

6

Reactant 3

HCID 871105-ChloroindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823776HCID 24823776, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloroindole (0.30 g. 2.0 mmol), ethylmagnesium bromide (1.0 M solution in THF, 2.4 mL, 2.4 mmol), zinc chloride (1.0 M solution in Et2O, 2.4 mL, 2.4 mmol) and the product of Example 1A (3.0 mmol) in 15 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.23 g, 0.85 mmol, 43% yield). MS (DCI/NH3) m/z 276 (M+H)+.

Sources & evidence

ORD record
ord-706036e7ff964266b4a0f04e5ffd5e2c
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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