Methanol → HCID 67995435, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 7-bromo-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (1.000 g, 3.80 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (0.319 g, 0.57 mmol), Palladium (II) acetate (0.128 g, 0.57 mmol) and Sodium acetate (0.623 g, 7.600) in a mixture of Methanol (30 mL) and DMA (10 mL) was degassed under vacuum and pressurized with Carbon Monoxide gas [CO] from a lecture bottle to approx. 55 psi in a sealed Steel Reaction vessel. The sealed vessel was heated at 95° C. overnight behind a protective shield. LC-MS showed complete reaction. The reaction mixture was filtered through a pad of CELITE® and the filtrate concentrated under vacuum. The residue was diluted with dichloromethane, filtered and the filtrate concentrated to give methyl-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate as a tan solid. [0.732 g product, 3.02 mmol, 85% yield]. The product had an HPLC Retention Time=2.192 min [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC COMBISCREEN® ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 243.06

Provenance & Evidence