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

HRID 2353530Notes

Reaction equation

HRID 2353530 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

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)+.

Sources & evidence

ORD record
ord-2de5c96210b244e3875340a0f1d626fd
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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