Potassium Phosphate, Tribasic → Methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(2-methylbut-3-en-2-yl)benzoate

HRID 404378

Reaktionsgleichung

[CH3:1][C:2]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1OS(C(F)(F)F)(=O)=O)[C:9]([O:11][CH3:12])=[O:10])([CH:4]=[CH2:5])[CH3:3].[F:24][C:25]1[C:26](B(O)O)=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:24][C:25]1[C:26]([C:15]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=2[C:2]([CH3:1])([CH:4]=[CH2:5])[CH3:3])=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

The reaction mixture of T45.3 (0.45 g, 1.3 mmol), 5-fluoro-2-methoxypyridin-4-ylboronic acid (0.55 g, 3.2 mmol), potassium phosphate (0.81 g, 3.8 mmol), S-phos (0.11 g, 0.26 mmol) and palladium acetate (0.03 g, 0.13 mmol) in DMF (1.5 mL) was purged with nitrogen three times. The resulting mixture was heated at 90° C. for 2 hours. The mixture was then purified by CombiFlash® silica gel chromatography, eluent with hexane/EtOAc, 9/1 to give T45.4. MS ESI (pos.) m/e: 330.2 (M+H)+. 1H NMR (400 MHz, CDCl3) δ ppm 8.26 (1H, d, J=1.8 Hz), 7.95 (1H, s), 7.90 (1H, dd, J=7.8, 1.8 Hz), 7.06 (1H, d, J=7.8 Hz), 6.59 (1H, d, J=4.9 Hz), 5.88-6.02 (1H, m), 4.75-4.85 (2H, m), 3.95 (3H, s), 3.94 (3H, s), 1.38 (3H, s), 1.36 (3H, s)

Aufarbeitung

customwas purged with nitrogen three times
customThe mixture was then purified by CombiFlash® silica gel chromatography, eluent with hexane/EtOAc, 9/1
customto give T45.4

Quellen und Nachweise

ORD-Eintrag: ord-9719b670fbc846709b061411a6e4504f
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08748462B2

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