HCID 67958265, compound → HCID 67960642, compound

HRID 1484648Notes

Reaction equation

HRID 1484648 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[C:16]3[C:17]([CH3:21])([CH3:20])[CH2:18][O:19][C:15]=3[C:14]([CH3:22])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-])=O>CCO.[Pd]>[CH3:20][C:17]1([CH3:21])[C:16]2[C:11]([O:10][C:7]3[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:12][CH:13]=[C:14]([CH3:22])[C:15]=2[O:19][CH2:18]1

Participants

4

Reactant 1

HCID 67958265HCID 67958265, compound2×

Product 1

HCID 67960642HCID 67960642, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Nitro-2-[(3,3,7-trimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]pyridine (Intermediate 28, 920 mg, 3.0 mmol) was dissolved in EtOH (13.5 mL) and stirred under hydrogen atmosphere (2 bar) in the presence of Pd/C 10% w/w (46 mg, 5% w/w) at room temperature for 30 minutes. The catalyst was filtered off, washed with THF and the resulting solution evaporated to dryness to afford an orange solid. The crude product was crystallized from MeOH to the title compound (565 mg) as a beige solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with THF
  3. customthe resulting solution evaporated to dryness
  4. customto afford an orange solid
  5. customThe crude product was crystallized from MeOH to the title compound (565 mg) as a beige solid

Sources & evidence

ORD record
ord-866fe89b315349688a0e6bd695d0c2ef
Source dataset
uspto-grants-2016_08
Patent number
US09422272B2

Reaction notes

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