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

HRID 1964069Notes

Reaction equation

HRID 1964069 reaction equation
C1(=O)C2C(=CC=CC=2)CN1.[N+:11]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[C:21](=[O:23])[N:20]([C@@H:24]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH2:39][CH3:40])[CH:31]=1)[CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:19]2)([O-:13])=[O:12].[H][H].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].C(OC1C=C([C@H](N)CS(C)(=O)=O)C=CC=1OC)C.C(OC1C=C([C@@H](N)CS(C)(=O)=O)C=CC=1OC)C>>[N+:11]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[C:21](=[O:23])[N:20]([CH:24]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH2:39][CH3:40])[CH:31]=1)[CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:19]2)([O-:13])=[O:12]

Participants

8

Reactant 7

HCID 10199PhthalimidineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 10195080(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamineHCID 11282264(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 58224189(S)-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-7-nitroisoindolin-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 513564097-Nitro-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindolin-1-one

Procedure

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.

Sources & evidence

ORD record
ord-81fba970aed74874b12551f12948dce9
Source dataset
uspto-grants-2013_04
Patent number
US08415485B2

Reaction notes

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