Water → Methyl Cinnoline-6-carboxylate

HRID 2079992Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[N:10][CH:9]=[C:8]2Cl)=[O:4].C([O-])=O.[Na+].C(N(CC)C(C)C)(C)C.O>CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[N:10][CH:9]=[CH:8]2)=[O:4]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-cinnoline-6-carboxylic acid methyl ester (192 mg, 0.863 mmol) in dimethylsulfoxide (30 mL) were added sodium formate (70 mg, 1.04 mmol), tetrakis(triphenylphosphine)palladium(0) (198 mg, 0.702 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.21 mmol), and the mixture was stirred for 1.5 hours at 90° C. After cooling to room temperature, water was added, ethyl acetate extraction was carried out, the organic layer was washed with water and brine, then, after drying over anhydrous sodium sulfate, the organic layer was evaporated. The resulting solid was washed with diethyl ether, then, purified by silica gel column chromatography (hexane-ethyl acetate), and the title compound (16 mg, 0.089 mmol, 10%) was obtained.

Workup

temperatureAfter cooling to room temperature
extractionethyl acetate extraction
washthe organic layer was washed with water and brine
dry with materialafter drying over anhydrous sodium sulfate
customthe organic layer was evaporated
washThe resulting solid was washed with diethyl ether
custompurified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-18099bcf1f2e4219982ff292adbaa9f4
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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