Toluene → HCID 67366556, compound

Participants

Reaction Steps

A mixture of toluene (1.8 mL), n-butanol (3 mL) and 2M Na2CO3 (3 mL) was degassed with a stream of nitrogen for 20 minutes. The mixture was transferred onto a degassed mixture of (S)-tert-butyl 3-(2-chloroquinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.300 g, 0.86 mmol), palladium tetrakistriphenyl phosphine (0.0718 g, 0.06 mmol) and 5-methyl-2-methoxyphenylboronic acid (0.143 g, 0.86 mmol) and the solution was heated at reflux. After 17 hours the reaction was cooled, diluted with water (20 mL), and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4), and concentrated. Silica chromatography (6:1-1:1 petroleum ether/ethyl acetate) gave the title compound as a colourless solid (0.329 g, 99%).

Provenance & Evidence