Water → HCID 11739485, compound

Temperature

0 °C

To a magnetically stirred solution of pyridinium chlorochromate (PCC) (0.90 g, 4.18 mmol), sodium acetate (0.38 g, 4.63 mmol), and 4 Å molecular sieves (0.38 g) in dichloromethane (DCM) (100 mL) at 0° C. under Ar atmosphere was added 2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-1-thiophen-2-yl-ethanol 6c (0.70 g mL, 2.01 mmol). The reaction mixture was stirred for 0.5 h at 0° C., then warmed to room temperature and stirred for 3 h. Water (100 mL) was added, and the aqueous phase was extracted with dichloromethane (100 mL). The combined organic layers were washed with water (2×100 mL), dried (MgSO4), and concentrated in vacuo to the crude product. The pure product was obtained by column chromatography over silica gel (80:20 dichloromethane/EtOAc, as eluent), which gave the title compound (0.26 g, 36%) as an off white solid. 1H NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 2.39 (s, 3H), 4.61 (s, 2H), 7.07 (m, 2H), 7.25 (d, J=7.7 Hz, 2H), 7.55 (m, 3H), 7.63 (d, J=3.7 Hz, 1H), 7.65 d, J=5.1 Hz, 1H), 7.77 (s, 1H). 13C NMR (100 MHz, CDCl3) δ 18.6, 21.5, 35.8, 112.9, 117.0, 121.7, 122.2, 127.8, 128.6, 128.6, 129.6, 131.8, 133.2, 134.9, 137.8, 142.8, 144.5, 144.9, 188.2. Mass spectrum m/e 347 (M+).

1. temperaturewarmed to room temperature
2. stirringstirred for 3 h
3. extractionthe aqueous phase was extracted with dichloromethane (100 mL)
4. washThe combined organic layers were washed with water (2×100 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo to the crude product
7. customThe pure product was obtained by column chromatography over silica gel (80:20 dichloromethane/EtOAc, as eluent), which

ORD record

ord-b7ab5f3b018c4e3cb5838ec90bda7ad4

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148353B2