HCID 90050656, compound → HCID 90050547, compound

HRID 931378Notes

Reaction equation

HRID 931378 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[C:14](=O)[C:13]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:12]=1[O:11]2>CO.[OH-].[OH-].[Pd+2]>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:14][C:13]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:12]=1[O:11]2

Participants

4

Reactant 1

HCID 90050656HCID 90050656, compound

Product 1

HCID 90050547HCID 90050547, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2′,3-dioxo-1′,2′-dihydro-3H-spiro[benzofuran-2,3′-pyrrolo[2,3-b]pyridine]-5-carboxylate (200 mg, 0.64 mmol) and 20 wt. % palladium hydroxide on carbon (40 mg) in MeOH (5 mL) is stirred under an atmosphere of hydrogen (50 psi) for 18 h. The reaction mixture is then filtered through a pad of Celite° and the filtrate is concentrated in vacuo. The residue is partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution. The layers are separated and the aqueous layer is further extracted with CH2Cl2 (2×). The combined organic extracts are dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound.

Workup

  1. filtrationThe reaction mixture is then filtered through a pad of Celite°
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  4. customThe layers are separated
  5. extractionthe aqueous layer is further extracted with CH2Cl2 (2×)
  6. dry with materialThe combined organic extracts are dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4d06caa33254e84ab828e528e2315bc
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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