1H-Indole, 4,5,6,7-tetrafluoro- → (4,5,6,7-tetrafluoro-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227430Notes

Reaction equation

HRID 227430 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.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]>ClCCl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]2[C:3]=1[C:4]([C:24]([CH:20]1[C:21]([CH3:23])([CH3:22])[C:19]1([CH3:27])[CH3:18])=[O:25])=[CH:5][NH:6]2

Participants

6

Reactant 3

HCID 1400511H-Indole, 4,5,6,7-tetrafluoro-HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823775(4,5,6,7-tetrafluoro-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 12%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,5,6,7-tetrafluoroindole (Matrix Scientific, 1.0 g. 5.3 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.4 mL, 6.4 mmol), zinc chloride (1.0 M solution in Et2O, 6.4 mL, 6.4 mmol) and the product of Example 1A (7.9 mmol) in 40 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.19 g, 0.61 mmol, 12% yield). MS (DCI/NH3) m/z 314 (M+H)+.

Sources & evidence

ORD record
ord-60128c5065574285ad7811353ab643a6
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

Loading…