Dichloromethane → Methyl 2 inverted exclamation mark-Oxo-1 inverted exclamation mark-[[2-(trimethylsilyl)ethoxy]methyl]-1 inverted exclamation mark,2 inverted exclamation mark,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3 inverted exclamation mark-pyrrolo[2,3-b]pyridine]-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (described in Intermediate 2) (22.0 g, 49.3 mmol), PdCl2(dppf).CH2Cl2 (2.012 g, 2.46 mmol), and sodium acetate (8.1 g, 99 mmol) in MeOH (150 mL) was pressurized to 300 psi of carbon monoxide and then heated at 85° C. for 72 h. The reaction mixture was allowed to cool then concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of heptane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=426.1 (M+1).

Provenance & Evidence