HCID 59226503, compound → HCID 59226443, compound

HRID 2192546Notes

Reaction equation

HRID 2192546 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:11]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:11]1

Participants

4

Reactant 1

HCID 59226503HCID 59226503, compound

Product 1

HCID 59226443HCID 59226443, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3-(3-nitropyridin-4-yl)cyclohex-2-enyl)isoindoline-1,3-dione (1.0 equiv.) in acetic acid (0.1 M) was added 10% Pd/C (0.2 equiv.) and the reaction was stirred under a H2 balloon. After 3 days, the reaction was filtered through Celite, washed with ethyl acetate and methanol, the filtrate was diluted with ethyl acetate and washed twice with sat. 2M Na2CO3. The organic phase was dried with magnesium sulfate, filtered and concentrated. The crude material was triturated with hexanes and ethyl acetate to afford 2-(3-(3-aminopyridin-4-yl)cyclohexyl)isoindoline-1,3-dione in 73% yield. LC/MS=322.2 (M+H), Rt=0.64 min.

Workup

  1. filtrationthe reaction was filtered through Celite
  2. washwashed with ethyl acetate and methanol
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed twice with sat. 2M Na2CO3
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was triturated with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-0eb693b1ce974f5da5207b097c303a2b
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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