Triethylamine → HCID 86656170, compound

Participants

Reaction Steps

To a mixture of 1-[8-(5-fluoropyridin-3-yl)quinolin-7-yl]ethanol (0.135 g, 0.503 mmol) (prepared in analogy to Example 7 step 1-4, using 5-fluoropyridin-3-ylboronic acid instead of (2-fluorophenypboronic acid as starting material) in methylene chloride (3 mL) was added triethylamine (0.105 mL, 0.755 mmol), followed by methanesulfonyl chloride (0.0487 mL, 0.629 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, then concentrated to dryness under reduced pressure. The crude mesylate was dissolved in N,N-dimethylformamide (2 mL) and treated with sodium azide (0.164 g, 2.52 mmol) at room temperature overnight. After diluting with ethyl acetate, the mixture was washed with water and brine, dried over magnesium sulfate and then evaporated to dryness. The crude product was used in the next step. LCMS calculated for C16H13FN5(M+H)+: m/z=294.1; found: 294.0.

Provenance & Evidence