HCID 89610459, compound → HCID 71576576, compound

HRID 1507691Notes

Reaction equation

HRID 1507691 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36])C1C=CC=CC=1>CCO.[Pd]>[CH3:25][N:23]([CH3:24])[C:22]([C:12]1[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:10]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 89610459HCID 89610459, compound

Product 1

HCID 71576576HCID 71576576, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (1.03 g, 1.94 mmol) was dissolved in EtOH and then treated with 10% Pd/C (37 mg). The reaction mixture was purged with N2 for 5 min then Hydrogen gas was bubbled through the mixture with stirring at RT for 1.5 h. The mixture was filtered through Celite and concentrated in vacuo. The residual yellow solid was triturated with Et2O to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (602 mg, 89%) as a white solid: m/z 349 (M+H)+ (ES+), 347 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.60 (s, 1H), 8.46 (s, 1H), 7.08-7.01 (m, 2H), 6.90-6.82 (m, 2H), 4.00 (q, J=7.0 Hz, 2H), 3.76 (s, 3H), 2.83 (br s, 6H), 0.99 (t, J=7.1 Hz, 6H).

Workup

  1. customThe reaction mixture was purged with N2 for 5 min
  2. customHydrogen gas was bubbled through the mixture
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe residual yellow solid was triturated with Et2O

Sources & evidence

ORD record
ord-6085f9cadb6845809188defd27567105
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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