Phthalimidine → 7-Nitro-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindolin-1-one

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Reaction Steps

In a particular embodiment, the isoindolin-1-one compound of Formula (I) is Compound (1), i.e., (1S)-7-nitro-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindolin-1-one, where X1 is nitro; each of X2 X3 and X4 is hydrogen; R3 is methyl; R1 is methoxy; and R2 is ethoxy. Referring to Scheme A below, Compound (1) can be prepared from reaction between Compound (2) (i.e., (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonyl-ethylamine) and Compound (3) (i.e., methyl 2-bromomethyl-6-nitrobenzoate) in the presence of an inorganic catalyst such as potassium carbonate and sodium hydrogen carbonate. In another embodiment, the (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonyl-ethylamine) is replaced with (1R)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonyl-ethylamine) to form (1N)-7-nitro-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindolin-1-one.

Provenance & Evidence