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

HRID 1481788Notes

Reaction equation

HRID 1481788 reaction equation
C([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([CH3:34])[CH:29]=[CH:28]3)[C:22]([O:35][CH3:36])=[C:21]([O:37]CC2C=CC=CC=2)[C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:37][C:21]1[C:22]([O:35][CH3:36])=[C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([CH3:34])[CH:29]=[CH:28]3)[NH:24][C:9](=[O:8])[C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 71284261benzyl 2,4-bis(benzyloxy)-5-methoxy-6-(1-methyl-1H-indol-5-yl)nicotinate

Product 1

HCID 712846174-hydroxy-5-methoxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 2,4-bis(benzyloxy)-5-methoxy-6-(1-methyl-1H-indol-5-yl)nicotinate (73 mg, 0.12 mmol) and 10% Pd/C (18 mg) in ethyl acetate (3.0 mL) was stirred for 2 h at room temperature under a hydrogen balloon. The mixture was then filtered. The filtrate was evaporated and the residue was triturated with ether to give 4-hydroxy-5-methoxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (27 mg, 69%).

Workup

  1. filtrationThe mixture was then filtered
  2. customThe filtrate was evaporated
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c322dc91faa84434a22779e4f7ff09d2
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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