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

HRID 227406Notes

Reaction equation

HRID 227406 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-bb3c40ecc3c54dbfb078fb3ca78c7597
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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