2-Methoxyethanol → 8-Chloro-3-(2-methoxyethoxy)-1,5-naphthyridine

HRID 40368

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([OH:12])=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][CH2:34][CH2:35]O.C1COCC1.CCOC(/N=N/C(OCC)=O)=O>CO.ClCCl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH2:35][CH2:34][O:33][CH3:32])=[CH:7]2

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottom flask under nitrogen environment was charged with 8-chloro-1,5-naphthyridin-3-ol (1.05 g, 5.8 mmol), 22.8 g of PS-Triphenylphosphine (loading: 2.2 mmol/g), 2-methoxyethanol (2.2 mL, 27.9 mmol), and THF (29.1 ml, 5814 mmol)/DCM (58.1 mL). Mixture cooled to 0° C. and to this was added DEAD (1.84 mL) dropwise via syringe. Reaction mixture allowed to stir at room temperature for 16 hours. Diluted with 50 mL of 10% MeOH/dichloromethane and resin bound reagent filtered. Filtrate concentrated under reduced pressure and purified by ISCO silica gel chromatography (10-30% EtOAc/Hexanes) to afford 8-chloro-3-(2-methoxyethoxy)-1,5-naphthyridine (770 mg, 55% yield) as white solid. MS [M+H]=238.9. Calc'd for C11H11ClN2O2=238.67.

Workup

customReaction mixture
filtrationfiltered
concentrationFiltrate concentrated under reduced pressure
custompurified by ISCO silica gel chromatography (10-30% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-2a7c7b4c25c94c59a4daa243e01bfd0c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Linked notes

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