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

HRID 2353516Notes

Reaction equation

HRID 2353516 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-7244fb1f7a874b64935f4fb4c4acf3dd
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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