Phthalimidine → 3-Ethoxy-1H-isoindole
Reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.F[B-](F)(F)F.[CH2:16]([O+](CC)CC)[CH3:17]>C(Cl)(Cl)Cl>[CH2:16]([O:10][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]=1)[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Scheme VIII shows the synthesis of a benzyl-protected isoindolin-1-one oxime intermediate 27. Isoindolinone 25 is alkylated with triethyloxonium tetrafluoroborate in chloroform to afford the 3-ethoxy-1H-isoindole 26, which is reacted with O-benzylhydroxylamine hydrochloride and sodium carbonate in ethanol, providing intermediate 27. Intermediate 27 can be coupled by Suzuki reaction with intermediates 3 or 6 as in Schemes I and II. Alternatively, intermediate 27 can be converted to the boronate ester intermediate 28 by reaction with bis(pinacolato)diboron in dioxane, using [1,1′-bis(diphenylphosphino)ferrocene]palladium(II)chloride dichloromethane complex. The boronate ester intermediate 28 can be coupled by Suzuki reaction with intermediates 1 or 5 as in Schemes I and II.
Sources & evidence
- ORD record
- ord-63bf89e8b90a40d981968c23f27da030
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491829B2
Reaction notes
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