methyl 1H-indole-5-carboxylate → HCID 24823930, compound

HRID 2353518Notes

Reaction equation

HRID 2353518 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[O:4].C([Mg]Br)C.[CH3:18][C:19]1([CH3:27])[C:21]([CH3:23])([CH3:22])[CH:20]1[C:24](Cl)=[O:25]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:24]([CH:20]1[C:21]([CH3:23])([CH3:22])[C:19]1([CH3:27])[CH3:18])=[O:25])=[O:4]

Participants

6

Reactant 3

HCID 2737635methyl 1H-indole-5-carboxylateHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 24823930HCID 24823930, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl-indole-5-carboxylate (Lancaster, 3.0 g, 17 mmol), ethylmagnesium bromide (1.0 M solution in THF, 21 mL, 21 mmol), zinc chloride (1.0 M solution in Et2O, 21 mL, 21 mmol) and the product of Example 1A (26 mmol) in 50 mL of dichloromethane were processed as described in Example 1B to provide the title compound (3.4 g, 11 mmol, 66% yield). MS (DCI/NH3) m/z 300 (M+H)+.

Sources & evidence

ORD record
ord-b63ca76cb66c47e1ac95d034acd8853a
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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