HCID 10192891, compound → HCID 10236174, compound

HRID 1836028Notes

Reaction equation

HRID 1836028 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:16]([N+:17]([O-])=O)=[CH:15][C:14]([OH:20])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1>CC(O)=O.CO.[Pd]>[NH2:17][C:16]1[C:10]2[O:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)=[CH:12][C:11]=2[CH:13]=[C:14]([OH:20])[CH:15]=1

Participants

4

Reactant 1

HCID 10192891HCID 10192891, compound

Product 1

HCID 10236174HCID 10236174, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

A solution of 99 (0.070 g, 0.29 mmol) in AcOH/MeOH was stirred under an atmosphere of H2 in the presence of 10% Pd/C. After TLC analysis indicated reaction was over, the reaction was filtered through Celite, concentrated and chromatographed on silica gel (MeOH/CH2Cl2 1:9) to yield 25 mg of the desired product: Mp=251-254° C.; 1H NMR (DMSO-d6) δ 9.76 (br s, 1 H), 8.65 (br s, 1 H), 7.71 (d, 2 H, J=8.5 Hz), 6.86 (s, 1 H), 6.84 (d, 2 H, J=8.7 Hz), 6.09 (d, 1 H, J=1.9 Hz), 6.02 (d, 1 H, J=1.9 Hz), 5.21 (s, 2 H); MS 242 (M+H)+.

Workup

  1. customreaction
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated
  4. customchromatographed on silica gel (MeOH/CH2Cl2 1:9)

Sources & evidence

ORD record
ord-9f0c716797c24882aab138372d77d607
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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