HCID 71284381, compound → HCID 71281812, compound

HRID 1481768Notes

Reaction equation

HRID 1481768 reaction equation
C([O:8][C:9]1[C:17]([C:18]2[NH:23][C:22](=[O:24])[C:21]([C:25]([O:27][CH3:28])=[O:26])=[C:20]([OH:29])[C:19]=2[CH2:30][CH3:31])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:32])C1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O.[Pd]>[CH2:30]([C:19]1[C:20]([OH:29])=[C:21]([C:25]([O:27][CH3:28])=[O:26])[C:22](=[O:24])[NH:23][C:18]=1[C:17]1[C:9]([OH:8])=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:32])[CH:12]=[CH:11]2)[CH3:31]

Participants

5

Reactant 1

HCID 71284381HCID 71284381, compound

Product 1

HCID 71281812HCID 71281812, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate (Example 373, step 1, 0.086 g, 0.20 mmol) in DCM (5 mL) and EtOAc (2 mL) was hydrogenated under a H2-filled balloon over Pd/C (10% Degussa type, 20 mg) until complete consumption of staring material was observed. The catalyst was filtered off and washed with DCM and EtOAc. The mother liquor was concentrated and the residue was purified by column chromatography (MeOH/DCM, 0-5% gradient). Methyl 5-ethyl-4-hydroxy-6-(4-hydroxy-1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate was obtained as a yellowish solid (0.0466 g, 68%).

Workup

  1. customuntil complete consumption of staring material
  2. filtrationThe catalyst was filtered off
  3. washwashed with DCM and EtOAc
  4. concentrationThe mother liquor was concentrated
  5. customthe residue was purified by column chromatography (MeOH/DCM, 0-5% gradient)

Sources & evidence

ORD record
ord-61149445777f4caa8bb9b1e07c4e119a
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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