Cesium carbonate → Methyl 4'-(4-bromo-5-chloropyridin-2-ylamino)-5'-methoxy-2'-methylbiphenyl-4-carboxylate

Temperatur

150 °C

Methyl 4′-amino-5′-methoxy-2′-methylbiphenyl-4-carboxylate generated in Step 1 (200 mg, 0.75 mmol), 2,4-dibromo-5-chloropyridine (222 mg, 0.82 mmol, 1.1 equiv), Pd2(dba)3 (17 mg, 0.02 mmol, 0.025 equiv.), xantphos (22 mg, 0.04 mmol, 0.05 equiv.), and Cs2CO3 (365 mg, 1.1 mmol, 1.5 equiv.) are added to THF (5 mL). The resulting mixture is bubbled with N2 gas for 5 minutes and then heated at 150° C. for 4 hours. After cooling to room temperature, the reaction mixture is diluted into EtOAc and washed with H2O. The EtOAc layer is dried over Mg2SO4 and concentrated in vacuo. Silica gel chromatography (hexanes-EtOAc) affords Methyl 4′-(4-bromo-5-chloropyridin-2-ylamino)-5′-methoxy-2′-methylbiphenyl-4-carboxylate;

1. customThe resulting mixture is bubbled with N2 gas for 5 minutes
2. temperatureAfter cooling to room temperature
3. additionthe reaction mixture is diluted into EtOAc
4. washwashed with H2O
5. dry with materialThe EtOAc layer is dried over Mg2SO4
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-3b5b71f4638b4f9fb1b3e2fe47cfd4df

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08377921B2