Hydrochloric Acid → 5-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1481780Notes

Reaction equation

C([O:5][C:6]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[CH:22]3)[C:16]([Cl:29])=[C:15]([O:30]C(C)(C)C)[C:7]=1[C:8]([O:10]C(C)(C)C)=[O:9])(C)(C)C.Cl.O1CCOCC1>>[Cl:29][C:16]1[C:15]([OH:30])=[C:7]([C:8]([OH:10])=[O:9])[C:6](=[O:5])[NH:18][C:17]=1[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[CH:22]2

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 71284713tert-butyl 2,4-di-tert-butoxy-5-chloro-6-(1-methyl-1H-indol-5-yl)nicotinate

Product 1

HCID 712820235-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 68.5%

Procedure

Following the procedure of Example 375 step 7, treatment of tert-butyl 2,4-di-tert-butoxy-5-chloro-6-(1-methyl-1H-indol-5-yl)nicotinate (27 mg, 0.055 mmol) with HCl in dioxane (4.0 M×1.0 mL, 4.0 mmol) provided 5-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (12 mg, 68%).

Sources & evidence

ORD record: ord-ab3efb1735484ff29873298050e9b0a8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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