1H-Indole, 6-methyl- → (6-methyl-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone

HRID 2353517Notes

Reaction equation

HRID 2353517 reaction equation
[CH3:1][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-]>[CH3:1][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 1379281H-Indole, 6-methyl-HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823778(6-methyl-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanoneYield 65.8%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-methylindole (1.0 g, 7.6 mmol), ethylmagnesium bromide (1.0 M solution in THF, 9.1 mL, 9.1 mmol), zinc chloride (1.0 M solution in Et2O, 9.1 mL, 9.1 mmol) and the product of Example 1A (11 mmol) in 25 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.3 g, 5.0 mmol, 65% yield). MS (DCI/NH3) m/z 256 (M+H)+.

Sources & evidence

ORD record
ord-cb11ea52cda44d14b920ccb1cdaf89da
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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