Potassium Phosphate, Tribasic → HCID 67356926, compound

Participants

Reaction Conditions

Reaction Steps

In a 500 ml pressure vessel, 6-chloro-1-cyclopropyl-1H-pyrrolo[3,2-c]pyridine (7A, 6.2 g, 32 mmol), 4-(prop-1-en-2-yl)benzamide (6.2 g, 39 mmol), palladium (II) acetate (0.29 g, 1.3 mmol), and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (2.2 g, 3.9 mmol) were added. Ground-up potassium phosphate tribasic (15 g, 45 mmol) was then added, followed by 1,4-dioxane (130 ml) and t-butanol (32 ml). The vessel was purged with nitrogen for 30 min, before being sealed and heated at 130° C. for 24 hr. After cooling, 250 ml of water and 250 ml EtOAc were successively added. The layers were separated, and the aqueous layer was extracted once more with 200 ml EtOAc. Combined organic layers were dried with Na2SO4, filtered, and concentrated. The crude product was purified by normal phase column chromatography eluting with EtOAc (10-40%) in hexanes. Product-containing fractions were combined and concentrated to obtain the product N-(1-cyclopropyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(prop-1-en-2-yl)benzamide (7B, 4.2 g, 41%) as a yellow solid.

Provenance & Evidence