Sodium Carbonate → HCID 58442808, Verbindung

Temperatur

80 °C

2-Bromofuran-3-carboxylic acid methyl ester (3.0 g, 15 mmol, 1.0 eq.), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.5 g, 15 mmol, 1.0 eq.), THF (150 mL) and Na2CO3 (30 mL, 60 mmol, 4.0 eq.) were combined. The mixture was degassed and purged with nitrogen (3×). PdCl2(PPh3)2 (0.3 g, 0.4 mmol, 0.03 eq.) was added, and the mixture was again degassed and purged with nitrogen (3×), then heated at 80° C. overnight. The mixture was then cooled and the layers were separated. The THF layer was diluted with EtOAc (150 mL), washed with saturated aqueous NaCl (80 mL) and dried over Na2SO4. The material was filtered and applied onto a silica gel column and purified by chromatography with PE/EtOAc (20:1 to 10:1) to yield 4-(3-methoxycarbonylfuran-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (3.5 g) as a white solid.

1. customThe mixture was degassed
2. custompurged with nitrogen (3×)
3. customthe mixture was again degassed
4. custompurged with nitrogen (3×)
5. temperatureThe mixture was then cooled
6. customthe layers were separated
7. additionThe THF layer was diluted with EtOAc (150 mL)
8. washwashed with saturated aqueous NaCl (80 mL)
9. dry with materialdried over Na2SO4
10. filtrationThe material was filtered
11. custompurified by chromatography with PE/EtOAc (20:1 to 10:1)

ORD-Eintrag

ord-ec15a4a9acee4949b613c9b22b64e48a

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08530663B2