Diethyl Ether → 4-Ethenyl-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile

HRID 638978Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].[CH2:22](OCC)[CH3:23]>COCCOC.O>[CH:22]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15])=[CH2:23]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile (280 mg, 1.28 mmol), potassium carbonate (885 mg, 6.4 mmole), tetrakis-triphenylphosphine (30 mg, 0.026 mmole) in DME/H2O (20 mL, 3:1) was added 2,4,6-trivinylcycloborane-pyridine complex (154 mg, 0.64 mmole). After stirring for 1 h at 90° C., another batch of tetrakis-triphenylphosphine (30 mg, 0.026 mmol) was added. After refluxing for another 1.5 h, the mixture contents were cooled down to room temperature and extrated with diethyl ether. The ether fractions were combined, concentrated and purified by column chromatography (silica, 0-10% ethyl acetate in hexane) to give the title compound as a light yellow solid (176 mg, 65%): LC/MS (ES) m/e 212 (M+H)+.

Workup

temperatureAfter refluxing for another 1.5 h
temperaturethe mixture contents were cooled down to room temperature
concentrationconcentrated
custompurified by column chromatography (silica, 0-10% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-9167a1cdaa2a497ba0125f0f4de0cd77
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691850B2

Reaction notes

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