Potassium Carbonate → (S)-3-bromo-7-(2-fluoropyridin-3-yl)-2',6'-dihydrospiro[chromeno[2,3-b]pyridine-5,3'-[1,4]oxazin]-5'-amine

Temperatur

80 °C

A vial was charged with 2-fluoropyridin-3-ylboronic acid (0.094 g, 0.667 mmol), PdCl2(dppf)-CH2Cl2-adduct (0.026 g, 0.032 mmol), (S)-3-bromo-7-iodo-2′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.300 g, 0.635 mmol), and potassium carbonate (0.351 g, 2.54 mmol). Dioxane (3.5 mL) and water (1.5 mL) were added. The vial was flushed with argon, sealed and heated to 80° C. for 1 hour. The reaction mixture was then diluted with EtOAc, dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography [0-80% (90:10:1 DCM/MeOH/NH4OH)/DCM] gave (S)-3-bromo-7-(2-fluoropyridin-3-yl)-2′,6′-dihydrospiro[chromeno[2,3-b]pyridine-5,3′-[1,4]oxazin]-5′-amine (0.202 g, 0.458 mmol)

1. customThe vial was flushed with argon
2. customsealed
3. additionThe reaction mixture was then diluted with EtOAc
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customPurification of the crude residue by column chromatography [0-80% (90:10:1 DCM/MeOH/NH4OH)/DCM]

ORD-Eintrag

ord-3f5d7004fddb48b0b48aa2a28dc8aaf0

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08497264B2