Methyl indole-7-carboxylate → 3-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-7-carboxylic Acid Methyl Ester

HRID 227414Notes

Reaction equation

HRID 227414 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)=[O:4].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-]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[C:10]2[C:24]([CH:20]1[C:21]([CH3:23])([CH3:22])[C:19]1([CH3:27])[CH3:18])=[O:25])=[O:4]

Participants

6

Reactant 3

HCID 676694Methyl indole-7-carboxylateHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 672703043-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-7-carboxylic Acid Methyl EsterYield 63.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl-indole-7-carboxylate (Maybridge, 1.0 g, 5.7 mmol), ethylmagnesium bromide (1.0 M solution in THF, 6.9 mL, 6.9 mmol), zinc chloride (1.0 M solution in Et2O, 6.9 mL, 6.9 mmol) and the product of Example 1A (7.4 mmol) in 25 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.1 g, 3.6 mmol, 63% yield). MS (DCI/NH3) m/z 300 (M+H)+.

Sources & evidence

ORD record
ord-385480160bd24261bf5d64e4dcb8a794
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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