Benzophenone imine → N-(5-(diphenylmethyleneamino)-2-methoxypyridin-3-yl)methanesulfonamide

温度

120 °C

To a 5 mL microwave reaction tube was added N-(5-bromo-2-methoxypyridin-3-yl)methanesulfonamide (0.208 g, 0.739 mmol), xantphos (Acros, 0.044 g, 0.077 mmol), Pd2dba3 (Aldrich, 0.034 g, 0.037 mmol), NaOtBu (Aldrich, 0.178 g, 1.85 mmol) and diphenylmethanimine (Aldrich, 0.130 mL, 0.776 mmol) in DMF (3 mL). The mixture was degassed by bubbling argon through for 5 min. The tube was heated in a microwave reactor (Biotage) at 120° C. for 30 min. The reaction mixture was partitioned between tris-HCl buffer (1 M, pH 7.0) (20 mL) and EtOAc (10 mL). The aqueous phase was extracted with EtOAc (20 mL). The combined organic phases were washed with saturated aqueous sodium chloride (20 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (50 g, eluent: EtOAc in hexanes 20% to 80%) to afford N-(5-(diphenylmethyleneamino)-2-methoxypyridin-3-yl)methanesulfonamide (0.109 g, 39% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.69-7.74 (m, 2H) 7.53 (d, J=2.35 Hz, 1H) 7.46-7.51 (m, 1H) 7.38-7.44 (m, 2H) 7.30-7.36 (m, 3H) 7.12-7.18 (m, 3H) 6.60 (s, 1H) 3.94 (s, 3H) 2.69 (s, 3H).

1. customThe mixture was degassed
2. customby bubbling argon through for 5 min
3. customThe reaction mixture was partitioned between tris-HCl buffer (1 M, pH 7.0) (20 mL) and EtOAc (10 mL)
4. extractionThe aqueous phase was extracted with EtOAc (20 mL)
5. washThe combined organic phases were washed with saturated aqueous sodium chloride (20 mL)
6. dry with materialThe organic phase was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by silica gel column chromatography (50 g, eluent: EtOAc in hexanes 20% to 80%)

ORDレコード

ord-c9dfe9456b1346a7ba2e3744948ed334

出典データセット

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08772480B2