Toluene → HCID 57985925, compound

Participants

Reaction Steps

To a RT suspension of 4-methoxy-1H-pyrrolo[2,3-b]pyridine (prepared as described in WO03/082289, 1.0 g, 6.75 mmol) in toluene (30 ml) at RT was added isopropyl magnesium chloride(1.5 M in THF, 4.95 ml, 7.43 mmol) dropwise. The resulting mixture was stirred at RT for 30 min and neat diethyl benzylidene malonate (1.82 ml, 8.10 mmol) was added dropwise. The reaction was stirred for 1 h then quenched by addition of a saturated solution of NH4Cl and diluted with H2O and EtOAc. The resulting white solid precipitate was filtered and dried affording 2-[(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (2.13 g). An additional 130 mg was isolated from the mother liquors, giving 85% combined yield.

Provenance & Evidence