2-Bromopropanedial → HCID 86700131, compound

To a solution of material from Example 112 (3.21 g, 12.19 mmol) in a mixture of THF (107 mL) and acetic acid (29 mL) is added 2-bromomalonaldehyde (3.29 g, 21.79 mmol). The resulting solution is stirred at room temp for 60 h. The reaction is diluted with water (71 mL) and the resulting slurry is stirred at room temp for 1.5 h. The slurry is extracted with EtOAc (3×300 mL), the organic layers combined, washed with brine (1×50 mL), dried over Na2SO4, filtered and evaporated to dryness. The resulting residue is purified by BIOTAGE® Silica gel chromatography on a 80 g Thompson Single Step silica cartridge using a linear gradient from 100% CHCl3 to 25% MeOH/CHCl3 over 9 column volumes to give 1.5 g (39%) of the title compound as an orange/yellow film, 1H NMR (500 MHz, methanol-d4) δ 9.65 (s, 1H), 7.97 (s, 1H), 4.49-4.37 (m, 1H), 3.93 (dd, J=13.9, 4.4 Hz, 1H), 3.72 (dd, J=14.0, 7.7 Hz, 1H), 1.45 (s, 914). LC/MS (Condition A): ret. T=2.46 min, (M+Na) 338.

1. stirringthe resulting slurry is stirred at room temp for 1.5 h
2. extractionThe slurry is extracted with EtOAc (3×300 mL)
3. washwashed with brine (1×50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated to dryness
7. customThe resulting residue is purified by BIOTAGE® Silica gel chromatography on a 80 g Thompson Single Step silica cartridge

ORD record

ord-fd0630a7009944e38eda754b6674c7fe

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169295B2