HCID 86654328, compound → HCID 58303857, compound

HRID 1404113Notes

Reaction equation

HRID 1404113 reaction equation
Cl.[CH3:2][N:3]([CH3:24])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[C:10](/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])[CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[N:8]([CH3:23])[CH:7]=1>CO.[Pd]>[CH3:24][N:3]([CH3:2])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[C:10]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[N:8]([CH3:23])[CH:7]=1

Participants

4

Reactant 1

HCID 86654328HCID 86654328, compound

Product 1

HCID 58303857HCID 58303857, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 25-2 (78.6 mg, 0.25 mmol) and Pd/C (5%, 50 mg) in MeOH was purged with nitrogen and hydrogen, and then the reaction was stirred at room temperature. After 6 h, the reaction mixture was filtered and concentrated to give the compound 25-3 as a pale yellow semi-solid (67 mg), which was used for the next step without purification. 1H NMR (CDCl, 300 MHz) δ (ppm) 6.82 (d, J=8.0 Hz, 1H), 6.64 (s, 1H), 6.37 (d, J=8.0 Hz, 1H), 3.93 (s, 3H), 3.87 (s, 3H), 3.28-3.34 (m, 2H), 2.99-3.05 (m, 2H), 2.57-2.69 (m, 4H), 2.35 (s, 6H).

Workup

  1. customwas purged with nitrogen and hydrogen
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0e07d2133a814db1a4ce1d812d88d803
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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