Triacetoxyperiodinane → Methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetate

To a mixture of methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (2.6 g, 5.18 mmol) in CH2Cl2 (100 mL) was added Dess-Martin Periodinane (2.196 g, 5.18 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate (500 mL), washed with sat. NaHCO3 solution (100 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (5-70% EtOAc/hexane) to afford desired methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-oxoacetate (1.7 g, 3.40 mmol, 65.6% yield) as off-white solid. 1H NMR (500 MHz, CDCl3) δ: 8.21 (t, J=1.7 Hz, 1H), 7.96 (dt, J=7.7, 1.3 Hz, 1H), 7.61-7.58 (m, 1H), 7.39 (t, J=7.9 Hz, 1H), 7.14 (s, 1H), 4.03 (s, 3H), 2.57 (s, 3H). LCMS (M+H)=501.0.

1. washwashed with sat. NaHCO3 solution (100 mL)
2. dry with materialdried (Na2SO4)
3. filtrationfiltered
4. concentrationconcentrated
5. customThe residue was purified by silica gel chromatography (5-70% EtOAc/hexane)

ORD record

ord-3b26c88afaf14d5996ebb1b2a700294e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906929B2