Methyl indole-6-carboxylate → 3-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carboxylic Acid Methyl Ester

HRID 2353514

Reaction equation

HRID 2353514 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[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:13]=[C:12]2[C:8]([C:9]([C:24]([CH:20]3[C:21]([CH3:23])([CH3:22])[C:19]3([CH3:27])[CH3:18])=[O:25])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 639844Methyl indole-6-carboxylateHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 248239313-(2,2,3,3-Tetramethyl-cyclopropanecarbonyl)-1H-indole-6-carboxylic Acid Methyl EsterYield 40%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl-indole-6-carboxylate (2.0 g, 11.4 mmol), ethylmagnesium bromide (1.0 M solution in THF, 14 mL, 14 mmol), zinc chloride (1.0 M solution in Et2O, 14 mL, 14 mmol) and the product of Example 1A (17 mmol) in 30 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.35 g, 4.5 mmol, 40% yield). MS (DCI/NH3) m/z 300 (M+H)+.

Sources & evidence

ORD record
ord-f3447f07f3014ab4b2185bcd30aede02
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Linked notes

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