6-methanesulfonyl-1H-indole → (6-Methanesulfonyl-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 2353527Notes

Reaction equation

HRID 2353527 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Mg]Br)C.[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24](Cl)=[O:25]>[Cl-].[Zn+2].[Cl-]>[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:24]([CH:20]3[C:21]([CH3:23])([CH3:22])[C:19]3([CH3:27])[CH3:18])=[O:25])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 27610676-methanesulfonyl-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824474(6-Methanesulfonyl-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 13%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

The 6-(methylsulfonyl)-1H-indole (Apollo Scientific, 1.0 g, 5.1 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.1 mL, 6.1 mmol), zinc chloride (1.0 M solution in Et2O, 6.1 mL, 6.1 mmol) and the product of Example 1A (7.7 mmol) were processed as described in Example 1B to provide the title compound (0.21 g, 0.66 mmol, 13% yield). MS (DCI/NH3) m/z 378 (M+H)+.

Sources & evidence

ORD record
ord-6ced44bebebe44759dfde79b0d4f667c
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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