4-Nitro-1H-indole → (4-Nitro-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 2353508Notes

Reaction equation

HRID 2353508 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].C([Mg]Br)C.[CH3:17][C:18]1([CH3:26])[C:20]([CH3:22])([CH3:21])[CH:19]1[C:23](Cl)=[O:24]>ClCCl.[Cl-].[Zn+2].[Cl-]>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([C:23]([CH:19]1[C:20]([CH3:22])([CH3:21])[C:18]1([CH3:26])[CH3:17])=[O:24])=[CH:7][NH:8]2)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1457664-Nitro-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823929(4-Nitro-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 8.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-nitroindole (1.0 g, 6.2 mmol), ethylmagnesium bromide (1.0 M in THF, 6.8 mL, 6.8 mmol), zinc chloride (1.0 M solution in Et2O, 6.8 mL, 6.8 mmol) and the product of Example 1A (6.8 mmol) in 15 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.15 g, 0.53 mmol, 8% yield). MS (DCI/NH3) m/z 287 (M+H)+.

Sources & evidence

ORD record
ord-644938072f0f40d489cceaa02e6e49d1
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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