5-Benzyloxy-6-methoxyindole → HCID 24823928, compound

HRID 2353524Notes

Reaction equation

HRID 2353524 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[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.[CH3:24][C:25]1([CH3:33])[C:27]([CH3:29])([CH3:28])[CH:26]1[C:30](Cl)=[O:31]>[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][CH3:19])[NH:14][CH:13]=[C:12]2[C:30]([CH:26]1[C:27]([CH3:29])([CH3:28])[C:25]1([CH3:33])[CH3:24])=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2608005-Benzyloxy-6-methoxyindoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823928HCID 24823928, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixture of 5-benzyloxy-6-methoxyindole (Sigma, 2.0 g, 7.9 mmol), ethylmagnesium bromide (1.0 M solution in THF, 9.5 mL, 9.5 mmol), zinc chloride (1.0 M solution in Et2O, 9.5 mL, 9.5 mmol) and the product of Example 1A (12 mmol) was processed as described in Example 1B to provide the title compound (2.0 g, 5.2 mmol, 66% yield). MS (DCI/NH3) m/z 378 (M+H)+.

Sources & evidence

ORD record
ord-47141dd3e1d242548ecbdeaf8006f6db
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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