Pyridine → Diisopropylethylamine
Reaction equation
[CH2:1](OCC)C.O1[CH2:10][CH2:9][CH2:8]C1.C(Cl)Cl.C(Cl)(Cl)Cl.[N:18]1[CH:23]=[CH:22]C=[CH:20][CH:19]=1>C(N(CC)CC)C>[CH:9]([N:18]([CH:19]([CH3:20])[CH3:1])[CH2:23][CH3:22])([CH3:10])[CH3:8]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
As shown in reaction Scheme G, treatment of 2-arylindole (17) with oxalyl chloride neat or in an inert organic solvent such as methylene chloride, chloroform, dichloroethane, tetrahydrofuran or the like at a temperature of 25°-65° C. for a period of 3-24 hours gives the acylchloride adduct (18). The crude product (18) may be reacted with an amine of type (19) in an inert organic solvent such as diethylether, tetrahydrofuran, methylene chloride, chloroform or the like and an amine base such as triethylamine, diisopropylethylamine or pyridine at a temperature of 0°-25° C. for a period of 30 minutes to 4 hours to provide the amide derivative (20). Amide (20) may be further modified by treatment with a reducing agent such as borane or lithium aluminum hydride in an inert organic solvent such as tetrahydrofuran at elevated temperatures, preferably reflux, for a period of 1-5 hours to give compound (21). ##STR12##
Sources & evidence
- ORD record
- ord-fe9548f8619c49d0980de624e8e4964b
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06017944
Reaction notes
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