HCID 67318563, compound → HCID 59427337, compound

HRID 1042826Notes

Reaction equation

HRID 1042826 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1.[H][H]>CO.[Pd].CCOC(C)=O>[N:9]1[C:10]2[CH2:11][CH2:2][CH2:3][NH:4][C:5]=2[C:6]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 67318563HCID 67318563, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59427337HCID 59427337, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(7-bromo-1,5-naphthyridin-4-yloxy)benzenamine (0.150 g, 0.474 mmol) in MeOH (7 mL) at RT was added a suspension of 10% palladium on carbon (0.0505 g, 0.474 mmol) in EtOAc (2 mL). The mixture was subjected to an atmosphere of hydrogen (balloon) and stirred overnight. After 18 hrs, the mixture was filtered over celite and concentrated in vacuo. The resulting tan foam, crude 4-(5,6,7,8-tetrahydro-1,5-naphthyridin-4-yloxy)benzenamine, was advanced without further purification. [email protected] min

Workup

  1. waitAfter 18 hrs
  2. filtrationthe mixture was filtered over celite and
  3. concentrationconcentrated in vacuo
  4. customThe resulting tan foam, crude 4-(5,6,7,8-tetrahydro-1,5-naphthyridin-4-yloxy)benzenamine, was advanced without further purification
  5. custom[email protected] min

Sources & evidence

ORD record
ord-8cf75dd43df24641b7d3ceef2e1f3886
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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