HCID 67958265, compound → HCID 67960642, compound

HRID 527645Notes

Reaction equation

HRID 527645 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 185, 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-7020565492c54ed4aa6c4fdb1d4ee1d4
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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