1,2-Dimethoxyethane → 8-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridine

HRID 638987

Reaction equation

Br[C:2]1[C:3]([F:14])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].CO[CH2:23][CH2:24]OC>O>[CH:23]([C:2]1[C:3]([F:14])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2)=[CH2:24]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 8-bromo-7-fluoro-2-(methyloxy)-1,5-naphthyridine (2.0 g, 7.81 mmol), potassium carbonate (1.08 g, 7.81 mmol), tetrakis-triphenylphosphine (90 mg, 0.08 mmol) in DME (60 mL) and H2O (20 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (0.94 g, 3.91 mmol). After stirring for 10 h at 85° C. the reaction contents were concentrated and the product purified by chromatography (silica, 25% EtOAc in hexane) to give the title compound as a low melting solid (1.43 g, 90%): MS (ES) m/z 206 (M+H)+.

Workup

customthe reaction contents
concentrationwere concentrated
customthe product purified by chromatography (silica, 25% EtOAc in hexane)

Sources & evidence

ORD record: ord-6263a4675a0d4126a05511a0be0bf496
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691850B2

Linked notes

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