1,4-Dioxane → Methyl 2-(5-(3-methylisoxazol-5-yl)furo[3,2-b]pyridin-3-yl)acetate

HRID 2176654

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]2[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]2=[CH:4][CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[CH3:50][C:51]1[CH:55]=[C:54]([Sn](CCCC)(CCCC)CCCC)[O:53][N:52]=1.O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C(Cl)Cl>[CH3:50][C:51]1[CH:55]=[C:54]([C:2]2[N:7]=[C:6]3[C:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:9][O:10][C:5]3=[CH:4][CH:3]=2)[O:53][N:52]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A sealable flask was charged with methyl 2-(5-chlorofuro[3,2-b]pyridin-3-yl)acetate, palladium (II) acetate (49.8 mg, 222 μmol), X-Phos (211 mg, 443 μmol), and 3-methyl-5-(tributylstannyl)isoxazole (1319 mg, 3546 μmol). The flask was sealed and dioxane (20 mL) was added. The mixture was sparged with N2 for 10 min, then heated at 100° C. for 48 h. The mixture was cooled to rt and concentrated for purification by MPLC (Teledine Isco combiFlash Companion). The crude residue was taken up in minimal CH2Cl2 and absorbed onto a 25 g loading cartridge and passed through a Redi-Sep®, pre-packed silica gel column (40 g) using 98:2 CH2Cl2:MeOH to 90:10 CH2Cl2: MeOH to afford methyl 2-(5-(3-methylisoxazol-5-yl)furo[3,2-b]pyridin-3-yl)acetate (581 mg, 96.3% yield). LRMS (ESI) m/z calcd for C4H113N2O4 (M+H) 273.1. found 273.3.

Aufarbeitung

customThe flask was sealed
customThe mixture was sparged with N2 for 10 min
temperatureThe mixture was cooled to rt
concentrationconcentrated for purification by MPLC (Teledine Isco combiFlash Companion)
customabsorbed onto a 25 g loading cartridge

Quellen und Nachweise

ORD-Eintrag: ord-52086ca3e46849b9b67564fb6bd3128a
Quelldatensatz: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09066954B2

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