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

HRID 227422Notes

Reaction equation

HRID 227422 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-ac68f1d99f984a599dd2ef45a38f794f
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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