Phthalimide → HCID 11609941, compound

HRID 2055136Notes

Reaction equation

HRID 2055136 reaction equation
CO[C:3](=O)[CH:4]=[CH:5][C:6]([N:9]1[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10]1)([CH3:8])[CH3:7].[H][H].[BH4-].[Na+].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:54]1(=[O:64])[NH:58][C:57](=[O:59])[C:56]2=[CH:60][CH:61]=[CH:62][CH:63]=[C:55]12>C1COCC1.[Pd]>[N:9]1([C:6]([CH3:7])([CH3:8])[CH2:5][CH2:4][CH2:3][N:58]2[C:54](=[O:64])[C:55]3[C:56](=[CH:60][CH:61]=[CH:62][CH:63]=3)[C:57]2=[O:59])[C:17]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10]1

Participants

9

Reactant 6

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4311764Sodium borohydrideHCID 69221745HCID 69221745, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11609941HCID 11609941, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-imidazo[4,5-b]pyridin-1-yl-4-methyl-pent-2-enoic acid methyl ester (1 eq) was added palladium, 10 wt. % on activated carbon, (10%) and left stirring under an atmospheric pressure of hydrogen for 2 days. After the catalyst was filtered off, the mixture was concentrated and dissolved in ethanol. To this solution was added sodium borohydride (4 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the solvent was removed in vacuto, a solution of the residue in dichloromethane was washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated. To a solution of the residue in THF was added dropwise diethyl azodicarboxylate (1 eq), triphenyl phosphine (1 eq), and phtalimide (1 eq). The yellow solution was stired at room temperature overnight and the solution was concentrated. The crude solid was treated with 3 N HCl and ethyl acetate. Once the aqueous layer was seperated, it was added to ethyl acetate and treated with sodium bicarbonate under vigorous stirring to obtain an approximate basic pH 7. The organic phase was seperated and washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated to give 2-(4-imidazol[4,5-b]pyridin-1-yl-4-methyl-pentyl)-isoindole-1,3-dione (40%). MH+(349)

Workup

  1. waitleft
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe mixture was concentrated
  4. dissolutiondissolved in ethanol
  5. customquenched by addition of H2O
  6. customOnce the solvent was removed in vacuto
  7. washa solution of the residue in dichloromethane was washed with NaCl (sat.)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. concentrationthe solution was concentrated
  12. additionThe crude solid was treated with 3 N HCl and ethyl acetate
  13. customOnce the aqueous layer was seperated
  14. additionit was added to ethyl acetate
  15. additiontreated with sodium bicarbonate
  16. customto obtain an approximate basic pH 7
  17. customThe organic phase was seperated
  18. washwashed with NaCl (sat.)
  19. dry with materialdried over sodium sulfate
  20. filtrationfiltered
  21. concentrationconcentrated

Sources & evidence

ORD record
ord-07ad2ef46b4f4aeba1edc0b72a92cbf9
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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