5,6-Bis(phenylmethoxy)-1H-indole → (5,6-Bis-benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227428노트

반응식

HRID 227428 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Br)C.[CH3:30][C:31]1([CH3:39])[C:33]([CH3:35])([CH3:34])[CH:32]1[C:36](Cl)=[O:37]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][CH:13]=[C:12]2[C:36]([CH:32]1[C:33]([CH3:35])([CH3:34])[C:31]1([CH3:39])[CH3:30])=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 209205,6-Bis(phenylmethoxy)-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 67269830(5,6-Bis-benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone수율 55%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6344Dichloromethane용매

실험 절차

The 5,6-dibenzyloxyindole (Sigma, 0.60 g, 1.8 mmol), ethylmagnesium bromide (1.0 M solution in THF, 2.2 mL, 2.2 mmol), zinc chloride (1.0 M solution in Et2O, 2.2 mL, 2.2 mmol) and the product of Example 1A (2.7 mmol) in 20 mL of dichloromethane were processed as described in Example 1B to provide the title compound (0.45 g, 0.99 mmol, 55% yield). MS (DCI/NH3) m/z 454 (M+H)+.

출처 및 근거

ORD 기록
ord-4ad9650b0f224fbe8fc495790ce41221
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560481B2

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