2-Methylindole → HCID 24824478, compound

HRID 227405Notes

Reaction equation

HRID 227405 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.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[NH:3][C:4]2[C:9]([C:10]=1[C:21]([CH:17]1[C:18]([CH3:20])([CH3:19])[C:16]1([CH3:24])[CH3:15])=[O:22])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 72242-MethylindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824478HCID 24824478, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methylindole (0.75 g, 5.7 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.6 mL, 6.6 mmol), zinc chloride (1.0 M solution in Et2O, 6.6 mL, 6.6 mmol) and the product of Example 1A (6.3 mmol) in 15 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.76 g, 3.0 mmol, 52% yield). MS (DCI/NH3) m/z 256 (M+H)+.

Sources & evidence

ORD record
ord-88d0dceea8a14865a49a0d2d91d79c6c
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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