Dimethyl Sulfoxide → HCID 58763619, compound

Temperature

-78 °C

A dry round bottom flask was charged with anhydrous CH2Cl2 (4 mL) and anhydrous DMSO (116 μL, 1.63 mmol) and cooled to −78° C. Oxalyl chloride (85 μL, 0.97 mmol) was added and the resulting clear solution was stirred at −78° C. for 1 h. 2-(6-Chloro-8-methyl-2-phenyl-imidazo[1,2-a]pyridin-3-yl)-ethanol 43b (233 mg, 0.81 mmol) was suspended in CH2Cl2 (2 mL) and added via syringe to the oxalyl chloride/DMSO mixture. After the resulting yellow/opaque solution had stirred at −78° C. for 1 h, N,N-diisopropylethylamine (Hunigs base) (705 mL, 4.06 mmol) was added. The solution was warmed to 0° C. and stirred for 2 h. Water (20 mL) was added and the crude reaction was washed with CH2Cl2 (2×30 mL). The organic washes were combined, dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel column chromatography with 30-80% EtOAc/hexanes to yield the title compound (64 mg, 28%) as an orange oil. 1H NMR (400 mHz, CDCl3) δ 9.74 (d, J=1.47 Hz, 1H), 7.77 (s, 1H), 7.63 (d, J=7.70 Hz, 2H), 7.46-7.35 (m, 4H), 7.00 (d, J=0.73 Hz, 1H), 4.09 (s, 2H), 2.63 (s, 3H); DEPT (100 mHz, CDCl3) CH3: 17.1, CH2: 39.6, CH: 196.0, 128.9, 128.8, 128.4, 125.1, 119.0. Mass spectrum (m/e) 285 (M+1)+.

1. stirringAfter the resulting yellow/opaque solution had stirred at −78° C. for 1 h
2. temperatureThe solution was warmed to 0° C.
3. stirringstirred for 2 h
4. customthe crude reaction
5. washwas washed with CH2Cl2 (2×30 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product was purified by silica gel column chromatography with 30-80% EtOAc/hexanes

ORD record

ord-80fc58ad251a44a1a0a04d3ecacb2fd7

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566725B2