5-Bromoindole → (5-Bromo-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 2353534Notes

Reaction equation

HRID 2353534 reaction equation
[Br: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-]>[Br: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 249055-BromoindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824342(5-Bromo-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 38%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromoindole (5.0 g. 26 mmol), ethylmagnesium bromide (1.0 M solution in THF, 31 mL, 31 mmol), zinc chloride (1.0 M solution in Et2O, 31 mL, 31 mmol) and the product of Example 1A (38 mmol) in 100 mL of dichloromethane was processed as described in Example 1B to provide the title compound (3.1 g, 9.8 mmol, 38% yield). MS (DCI/NH3) m/z 321, 322 (M+H)+.

Sources & evidence

ORD record
ord-25a896f8546f48c5ad2c040e1672461c
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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