Cesium carbonate → HCID 59186352, Verbindung

Temperatur

180 °C

A suspension of 5-bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine (69.2 mg, 0.325 mmol, 1 equiv), 4-methoxypiperidine (150 mg, 1.3 mmol, 4.0 equiv), cesium carbonate (212 mg, 0.652 mmol, 2.00 equiv), XPhos (16.9 mg, 0.0354 mmol, 0.109 equiv), and tris(dibenzylideneacetone)dipalladium (0) (9.3 mg, 0.010 mmol, 0.031 equiv) in N,N-dimethylformamide (2 mL) was heated to 180° C. in the microwave for 15 min. The reaction mixture was concentrated in vacuo. The resulting residue was partitioned between ethyl acetate (5 mL) and saturated aqueous sodium chloride solution (5 mL). The aqueous was extracted with ethyl acetate (2×5 mL). The combine organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromotagraphy (95:5 dichloromethane/methanol) afforded a white solid (557 mg, 67%). LCMS (ESI) m/z: 248.3. NMR (500 MHz, CDCl3), δ: 7.32 (m, 1H), 7.05 (m, 1H), 6.23 (m, 1H), 4.39 (br s, 2H), 3.66 (m, 2H), 3.48 (m, 1H), 3.41 (s, 3H), 3.18 (m, 2H), 2.08 (m, 2H), 1.89 (m, 2H).

1. concentrationThe reaction mixture was concentrated in vacuo
2. customThe resulting residue was partitioned between ethyl acetate (5 mL) and saturated aqueous sodium chloride solution (5 mL)
3. extractionThe aqueous was extracted with ethyl acetate (2×5 mL)
4. dry with materialThe combine organic was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification by flash column chromotagraphy (95:5 dichloromethane/methanol)

ORD-Eintrag

ord-f35e097a1ff5487da5b8e60e39d33109

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889673B2