Hydrochloric Acid → HCID 86669350, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,4-dihydroxy-5-nitrobenzaldehyde (1.0 g, 5.46 mmol) in dry DMF (10 mL) was added Cs2CO3 (3563 mg, 10.93 mmol), NaI (819 mg, 5.46 mmol) and 2-bromopropane (1009 mg, 8.20 mmol) and the mixture was stirred at 60° C. overnight. The mixture was cooled to room temperature and added 1N HCl till pH=7, followed by a standard aqueous/EtOAc workup. The residue was purified by silica gel column chromatography (DCM:THF=20:1) to give Intermediate 49 as a yellow solid (230 mg, 18.7%). 1H NMR (DMSO-d6 500 MHz TMS): δ 9.86 (s, 1H), 8.08 (s, 1H), 7.65 (s, 1H), 4.79 (m, 1H), 1.28 (d, J=6.5 Hz, 6H).

Provenance & Evidence