7-(Benzyloxy)-1H-indole → (7-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanone

HRID 227411

Reaction equation

HRID 227411 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]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:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[C:28]([CH:24]1[C:25]([CH3:27])([CH3:26])[C:23]1([CH3:31])[CH3:22])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2607987-(Benzyloxy)-1H-indoleHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24824476(7-Benzyloxy-1H-indol-3-yl)-(2,2,3,3-tetramethyl-cyclopropyl)-methanoneYield 40%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-benzyloxyindole (Matrix Scientific, 2.0 g, 9.0 mmol), ethylmagnesium bromide (1.0 M solution in THF, 11 mL, 11 mmol), zinc chloride (1.0 M solution in Et2O, 11 mL, 11 mmol) and the product of Example 1A (13.4 mmol) in 30 mL of dichloromethane was processed as described in Example 1B to provide the title compound (1.3 g, 3.6 mmol, 40% yield). MS (DCI/NH3) m/z 348 (M+H)+.

Sources & evidence

ORD record
ord-ecde1ad6124448cb93b342494b888b95
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Linked notes

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