Hydrochloric Acid → HCID 71284206, compound

HRID 1481769Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([OH:25])=[C:5]([C:21]([O:23]C)=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[C:10]([OH:19])=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2)[CH3:2].[Li+].[I-].Cl>CCOC(C)=O>[CH2:1]([C:3]1[C:4]([OH:25])=[C:5]([C:21]([OH:23])=[O:22])[C:6](=[O:20])[NH:7][C:8]=1[C:9]1[C:10]([OH:19])=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[CH:13]=[CH:12]2)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 5-ethyl-4-hydroxy-6-(4-hydroxy-1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (0.045 g, 0.12 mmol) in EtOAc (1.0 mL) was added LiI (0.050 g, 0.37 mmol). The reaction mixture was stirred and heated at 60° C. for 1 h until complete consumption of starting material was observed. The mixture was then cooled to room temperature and acidified with aqueous HCl (1M, 1.0 mL) to pH˜2. The product was extracted with EtOAc (3×5 mL). The organic phase was dried over Na2SO4. Upon removal of the solvent the residue was triturated with Et2O. The solid was collected by filtration affording product (0.018 g, 42%) as a solid.

Workup

temperatureThe mixture was then cooled to room temperature
extractionThe product was extracted with EtOAc (3×5 mL)
dry with materialThe organic phase was dried over Na2SO4
customUpon removal of the solvent the residue
customwas triturated with Et2O
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-e5589ba1bbec40dc9b7848ce2845cc4a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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