Indole → HCID 44626730, compound

HRID 227407Notes

Reaction equation

HRID 227407 reaction equation
[F:1][C:2]1([F:12])[C:5]([F:7])([F:6])[CH2:4][C:3]1([CH3:11])[C:8](Cl)=[O:9].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.C([Mg]Br)C>ClCCl.[Cl-].[Zn+2].[Cl-]>[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:8]([C:3]2([CH3:11])[CH2:4][C:5]([F:7])([F:6])[C:2]2([F:12])[F:1])=[O:9])=[CH:14]1

Participants

6

Reactant 3

HCID 798IndoleHCID 533989902,2,3,3-Tetrafluoro-1-(methyl)cyclobutanecarbonyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 44626730HCID 44626730, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2,3,3-tetrafluoro-1-(methyl)-cyclobutanecarbonyl chloride (ABCR, 1.0 g, 4.9 mmol), indole (0.57 g, 4.9 mmol), ethylmagnesium bromide (1.0 M solution in THF, 5.4 ml, 5.4 mmol) and zinc chloride (1.0 M solution in Et2O, 5.4 mL, 5.4 mmol) in 50 mL of dichloromethane was processed as described in Example 1B to provide the title compound (0.40 g, 1.4 mmol, 29% yield). MS (DCI/NH3) m/z 286 (M+H)+.

Sources & evidence

ORD record
ord-16657cd471ef4025b57d183fb6713b21
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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