4-(phenylmethoxy)-1H-indole → (4-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227413

반응식

HRID 227413 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.[CH3:22][C:23]1([CH3:31])[C:25]([CH3:27])([CH3:26])[CH:24]1[C:28](Cl)=[O:29]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:28]([CH:24]1[C:25]([CH3:27])([CH3:26])[C:23]1([CH3:31])[CH3:22])=[O:29])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 884654-(phenylmethoxy)-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 24823779(4-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone수율 34%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-benzyloxyindole (1.1 g, 4.8 mmol), ethylmagnesium bromide (1.0 M solution in THF, 5.2 mL, 5.2 mmol), zinc chloride (1.0 M solution in Et2O, 5.2 mL, 5.2 mmol) and the product of Example 1A (4.8 mmol) in 25 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.56 g, 1.6 mmol, 34% yield). MS (DCI/NH3) m/z 348 (M+H)+.

출처 및 근거

ORD 기록
ord-470c9d5964914cd6b26f18ed997b77b9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560481B2

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