تفاعل #683244
ord-e8b865acecab4916b4cf06e0058c4bce
معادلة التفاعل
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المذيبات
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المعالجة
- 1أخرىThe mixture was purged with argon
- 2أخرىThe mixture was purged with argon
- 3أخرىsealed
- 4أخرىThe DME layer of the reaction mixture was collected
- 5أخرىthe solid precipitates
- 6أخرىwere triturated with methanol (2×10 mL)
- 7تركيزconcentrated
- 8أخرىThe solid residue was partitioned between EtOAc (20 mL) and aq. HCl (1 N, 20 mL)
- 9تركيزThe aqueous layer was concentrated under reduced pressure
- 10أخرىthe obtained light yellow solid was triturated with methanol (8 mL)
- 11أخرىThe supernant was isolated via filtration
- 12تركيزconcentrated
الإجراء التجريبي
To a microwave vial were charged with 3-bromo-5-(tetrahydro-2H-pyran-4-yl)pyridin-2-amine (500 mg, 1.95 mmol), 4-borono-2-fluorobenzoic acid (1.07 g, 5.83 mmol), aqueous Na2CO3 (2 M, 4.86 mL) and DME (10 mL). The mixture was purged with argon, then followed by addition of Pd(PPh3)4 (225 mg, 0.194 mmol). The mixture was purged with argon, sealed and heated via microwave reactor at 125° C. for 20 min, and then at 130° C. for another 40 min. The DME layer of the reaction mixture was collected, and the solid precipitates were triturated with methanol (2×10 mL). Methanol supernatants were combined with DME layer, and concentrated. The obtained residue was stirred with Et2O (2×60 mL), and the Et2O supernatants were discarded. The solid residue was partitioned between EtOAc (20 mL) and aq. HCl (1 N, 20 mL). The EtOAc layer was stripped with 1N HCl (2×5 mL), and the aqueous layers were combined. The aqueous layer was concentrated under reduced pressure, and the obtained light yellow solid was triturated with methanol (8 mL). The supernant was isolated via filtration and concentrated. 4-(2-Amino-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)-2-fluorobenzoic acid (0.844 g, 2.67 mmol, 137% yield) was obtained as light yellow foam. LCMS (m/z) 317.2 (MH+) 0.46 min.