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

HRID 1441250Notes

Reaction equation

HRID 1441250 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

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 454803208-Bromo-7-fluoro-2-methoxy-1,5-naphthyridine

Product 1

HCID 575995778-Ethenyl-7-fluoro-2-(methoxy)-1,5-naphthyridineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 mmole), tetrakis-triphenylphosphine (90 mg, 0.08 mmole) in DME (60 mL) and H2O (20 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (0.94 g, 3.91 mmole). After stirring for 10 hours at 85° C. the reaction contents were concentrated and the product purified by chromatography on silica gel (hexanes/EtOAc, 4:1) to give a low melting solid (1.43 g, 90%).

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated
  3. customthe product purified by chromatography on silica gel (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-f871cc9dbe3142b2abc510930efd34c0
Source dataset
uspto-grants-2010_02
Patent number
US07655648B2

Reaction notes

Loading…