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

HRID 227412

反応式

HRID 227412 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6344Dichloromethane溶媒

実験手順

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)+.

出典と根拠

ORDレコード
ord-845082f05d9a4e1696ef1f36e0648b77
出典データセット
uspto-grants-2009_07
特許番号
US07560481B2

関連ノート

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