Asymmetric syntheses for spiro-oxindole compounds useful as therapeutic agents
US-9487535-B2 · Nov 8, 2016 · US
US10072020B1 · US · B1
| Field | Value |
|---|---|
| Publication number | US-10072020-B1 |
| Application number | US-201815957867-A |
| Country | US |
| Kind code | B1 |
| Filing date | Apr 19, 2018 |
| Priority date | Apr 3, 2018 |
| Publication date | Sep 11, 2018 |
| Grant date | Sep 11, 2018 |
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An isatin spiro compound having the following formula (I): R 1 is halogen or C 1-3 alkyl; R 2 is C 1-3 alkyl or benzyl; and R 3 and R 3′ are independently H, C 1-3 alkyl or phenyl.
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What is claimed is: 1. An isatin spiro compound having the following formula (I): wherein R 1 is halogen or C 1-3 alkyl; R 2 is C 1-3 alkyl or benzyl; and R 3 and R 3′ are independently H, C 1-3 alkyl or phenyl. 2. The isatin spiro compound of claim 1 , wherein R 1 is Cl or Br. 3. The isatin spiro compound of claim 1 , wherein R 2 is methyl, ethyl, propyl, or benzyl. 4. The isatin spiro compound of claim 1 , wherein R 3 and R 3′ are independently H or phenyl. 5. The isatin spiro compound of claim 1 , wherein the compound is selected form the group consisting of: 6. A method of preparing the isatin spiro compound of claim 1 comprising: reacting a compound of formula (II) with a compound of formula (III) and a compound of formula (IV) in a one pot reaction, wherein R 1 is halogen or C 1-3 alkyl; R 2 is C 1-3 alkyl or benzyl; and R 3 and R 3′ are independently H, C 1-3 alkyl or phenyl; wherein the non-polar solvent is selected from the group consisting of benzene, CCl 4 , toluene, and THF; and wherein the catalyst includes a strong acid cation exchange resin, ferrocene, and palladium acetate. 7. The method of the claim 6 , wherein a molar ratio of the compound of formula (II) to the compound of formula (III) is 1:1 to 1:1.5. 8. The method of the claim 6 , wherein a molar ratio of the compound of formula (II) to the compound of formula (IV) is 1:1 to 1:1.2. 9. The method of claim 6 , wherein the strong acid cation exchange resin includes a 7% crosslinked styrene divinylene copolymer with sulfonic acid group (—SO 3 H).
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