Binap, (A+-)- → HCID 66931012, compound

Participants

Reaction Steps

1,1-Dimethylethyl 2-(4-piperidinyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 49) (65 mg, 0.21 mmol), 5-bromo-2-methylpyridine (52 mg, 0.30 mmol), palladium acetate (5 mg, 0.02 mmol), (+/−) BINAP (25 mg, 0.04 mmol), sodium tert-butoxide (39 mg, 0.041 mmol) and dioxane (2 ml) were mixed and heated to reflux under Argon and kept at this temperature for 14 h. After an additional 1.5 h, more 5-bromo-2-methylpyridine (1.5 eq), palladium acetate (0.1 eq), (+/−) BINAP (0.2 eq) and sodium tert-butoxide (2 eq) were added and the mixture stirred at reflux under Argon for an additional 7 h. the mixture was then allowed to cool over 45 mins and was then diluted with methanol and purified by SCX eluting with methanol, then 2M methanol/NH3. Purified further by SPE(Si) eluting with dichloromethane:methanol 50:1→25:1→10:1. Further purification by Mass Directed Autopreparation afforded the title compound (D50). MS (ES+) m/e 412 [M+H]+.

Provenance & Evidence