Methoxymethyl-triphenylphosphonium chloride → HCID 69423758, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (methoxymethyl)triphenylphosphonium chloride (3.6 g, 10.5 mmol, 2.1 equiv) and potassium t-butoxide (2.48 g, 22 mmol, 4.4 equiv) was stirred 1 hour at 25° C. before a suspension of t-butyl 5-formyl-2-(2-oxo-1,2-dihydroquinolin-3-yl)-1H-indole-1-carboxylate (5-8, 1.94 g, 5.0 mmol, 1 equiv) in THF (100 mL) was added via canula and the resulting mixture was stirred at 25° C. for 18 hours. The reaction was concentrated and the residue was stirred in saturated NH4Cl solution. The insoluble solid was collected by filtration and sonicated in EtOAc and then water to give 3-{5-[2-methoxyethenyl]-1H-indol-2-yl}quinolin-2(1H)-one (10-1) as a 1:1 mixture of E and Z isomers. MS(M+1)=317.1

Provenance & Evidence