HCID 86725313, compound → HCID 86725315, compound

HRID 925202Notes

Reaction equation

HRID 925202 reaction equation
Cl.[CH2:2]([O:4][C:5]([N:7]1[CH2:27][CH2:26][C:11]2[C:12]3[C:13]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)=[CH:14][CH2:15][C:16]=3[C:17](I)=[CH:18][C:10]=2[CH2:9][CH2:8]1)=[O:6])[CH3:3].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[CH2:2]([O:4][C:5]([N:7]1[CH2:27][CH2:26][C:11]2[C:12]3[CH:13]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:14][CH2:15][C:16]=3[CH:17]=[CH:18][C:10]=2[CH2:9][CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 86725313HCID 86725313, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86725315HCID 86725315, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Into a 500 ml Parr hydrogenation bottle, the product from step (b) (0.38 mmol) dissolved in EtOH (50 ml) was added. To the argon purged bottle, 100 mg of 20% Pd(OH)2 was placed. The bottle was shaken over hydrogen (50 psi) for 6 h. The reaction mixture was filtered through celite and solvent evaporated in vacuo. The residue was dissolved in DCM and washed with saturated aqueous Na2CO3. The DCM layer was dried over Na2SO4 and solvent was evaporated in vacuo to give the crude product that was purified by silica-gel chromatography (gradient elution: 0 to 80% EtOAc in hexane) to give the sub-title compound as a yellow oil (70 mg). MS: ESI (positive): 337 (M+1).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through celite and solvent
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed with saturated aqueous Na2CO3
  6. dry with materialThe DCM layer was dried over Na2SO4 and solvent
  7. customwas evaporated in vacuo
  8. customto give the crude product that
  9. customwas purified by silica-gel chromatography (gradient elution: 0 to 80% EtOAc in hexane)

Sources & evidence

ORD record
ord-1c762f3093ff48b9bc06bb98879e4f02
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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