6-Bromoindole → (6-Bromo-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227434Notes

Reaction equation

HRID 227434 reaction equation
[Br: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-]>[Br: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 6764936-BromoindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824343(6-Bromo-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 44%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromoindole (2.0 g. 10 mmol), ethylmagnesium bromide (1.0 M solution in THF, 12 mL, 12 mmol), zinc chloride (1.0 M solution in Et2O, 12 mL, 12 mmol) and the product of Example 1A (15 mmol) in 50 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.4 g, 4.4 mmol, 44% yield). MS (DCI/NH3) m/z 320, 322 (M+H)+.

Sources & evidence

ORD record
ord-695a89822c2d4815abc64e385d33fa87
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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