HCID 59226459, compound → HCID 59226506, compound

HRID 2192549Notes

Reaction equation

HRID 2192549 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:7][CH:6]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:5]=[C:4]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[N+:25]([O-])=O)[CH2:3]1>C(O)(=O)C.[Pd]>[NH2:25][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:19]=1[C:4]1[CH2:3][C:2]([CH3:28])([CH3:1])[CH2:7][CH:6]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH:5]=1

Participants

4

Reactant 1

HCID 59226459HCID 59226459, compound

Product 1

HCID 59226506HCID 59226506, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-(5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1 eq) in acetic acid (0.1 M) was purged with nitrogen for 10 min. Then 10% Pd/C (0.10 eq) was added. The reaction mixture was stirred at room temperature overnight under an atmosphere of hydrogen. Solids were removed by filtration over celite, then rinsed with EtOAc and MeOH. The filtrate was concentrated, diluted with EtOAc and washed 2× with sat. aq. 2M Na2CO3. The organic layer was dried with MgSO4, filtered, and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 2-(3-(3-aminopyridin-4-yl)-5,5-dimethylcyclohex-2-enyl)isoindoline-1,3-dione (89%). LC/MS (m/z): MH+=348.3, Rt=0.79.

Workup

  1. customSolids were removed by filtration over celite
  2. washrinsed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with EtOAc
  5. washwashed 2× with sat. aq. 2M Na2CO3
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-4d7ac1b0eb7e4940a379ec0d5ab0874a
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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