Potassium Carbonate → HCID 20742778, compound

HRID 1884602Notes

Reaction equation

F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-])=O)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][N:20]=1)=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl.[Pd]>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[C:23]([O:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([NH2:12])=[CH:4][CH:3]=2)[CH:22]=[CH:21][N:20]=1)=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-fluoro-4-nitro-naphthalene (1.0 g, 5.24 mmol) in dry DMF (22 mL) was added 4-hydroxy-pyridine-2-carboxylic acid methyl ester (0.993 g, 5.24 mmol) and K2CO3 (7.24 g, 52.4 mmol). The resulting yellow suspension was stirred at 100° C. under argon for five h. After cooling to room temperature, the solution was diluted with CH2Cl2 (62 mL) and 10% Pd/C (1 g) was added. The suspension was stirred under a H2 balloon for 72 h. The reaction was then filtered through a plug of diatomaceous earth and rinsed with EtOAc (150 mL) and extracted with H2O (3×100 mL), brine (1×100 mL) and dried over MgSO4. The solvent was removed via rotary evaporation and the resulting oil was applied to a flash silica column eluting with MeOH:CH2Cl2 (2:98) to provide the title compound (800 mg, 52%).

Workup

temperatureAfter cooling to room temperature
additionwas added
stirringThe suspension was stirred under a H2 balloon for 72 h
filtrationThe reaction was then filtered through a plug of diatomaceous earth
washrinsed with EtOAc (150 mL)
extractionextracted with H2O (3×100 mL), brine (1×100 mL)
dry with materialdried over MgSO4
customThe solvent was removed via rotary evaporation
washeluting with MeOH:CH2Cl2 (2:98)

Sources & evidence

ORD record: ord-01fe91addc1747b285336a1b9ec22607
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06765009B2

Reaction notes

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