Sodium Carbonate → HCID 68290686, Verbindung

Temperatur

135 °C

Tetrakis(triphenylphosphine)palladium (0.046 g, 0.039 mmol) was added to a solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.1 g, 0.394 mmol), 3-iodo-1-methyl-1H-pyrazole (0.123 g, 0.592 mmol) and sodium carbonate (0.125 g, 1.183 mmol) in DME/H2O 3/1 (2.00 mL). The reaction mixture was heated for 1 hour at 135° C. under microwave irradiation before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to afford the title product as a yellow solid (60 mg, 73%). 1H NMR (500 MHz, CDCl3): δ 3.93 (s, 3H), 4.09 (br s, 2H), 6.42 (d, J=2.3 Hz, 1H), 6.79 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.3 Hz, 1H), 7.50 (dd, J=8.3, 2.0 Hz, 1H), 7.71 (d, J=2.0 Hz, 1H). LC (Method B)-MS (ESI, m/z) tR 2.35 min, 208 [(M+H+), 100%].

1. customquenched with water
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with EtOAc
4. dry with materialThe combined organic layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude mixture was purified via Biotage silica gel column chromatography
8. washeluting with (Cyclohexane/EtOAc 80/20 to 60/40)

ORD-Eintrag

ord-0c4084c43985405ea2c7a5aaeafb40e7

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09371319B2