benzyl 2,4-bis(benzyloxy)-5-ethyl-6-(6-methoxy-1H-indol-2-yl)nicotinate → 5-ethyl-4-hydroxy-6-(6-methoxy-1H-indol-2-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1481791Notes

Reaction equation

HRID 1481791 reaction equation
C([O:8][C:9]1[N:24]=[C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([O:34][CH3:35])[CH:28]=3)[C:22]([CH2:36][CH3:37])=[C:21]([O:38]CC2C=CC=CC=2)[C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[CH2:36]([C:22]1[C:21]([OH:38])=[C:10]([C:11]([OH:13])=[O:12])[C:9](=[O:8])[NH:24][C:23]=1[C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[C:29]([O:34][CH3:35])[CH:28]=2)[CH3:37]

Participants

5

Reactant 1

HCID 71284904benzyl 2,4-bis(benzyloxy)-5-ethyl-6-(6-methoxy-1H-indol-2-yl)nicotinate

Product 1

HCID 712845775-ethyl-4-hydroxy-6-(6-methoxy-1H-indol-2-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 34.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The intermediate obtained in Step 4 (170 mg, 0.24 mmol) was dissolved in a mixed solvent of MeOH (0.5 mL) and ethyl acetate (2.0 mL) and hydrogenated with 10% Pd on charcoal (50 mg) using a balloon at room temperature. LC/MS showed complete conversion was achieved overnight. The catalyst was filtered over Celite and washed with 5% MeOH in DCM. The filtrate was concentrated to dryness and the residue was triturated with DCM and dried to provide the title compound as a pale yellow powder (27 mg) in 34% yield.

Workup

  1. customat room temperature
  2. filtrationThe catalyst was filtered over Celite
  3. washwashed with 5% MeOH in DCM
  4. concentrationThe filtrate was concentrated to dryness
  5. customthe residue was triturated with DCM
  6. customdried

Sources & evidence

ORD record
ord-127497b79c0d48f1bef32d74728d3a1a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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