Electric Literature of 956434-30-3, A common heterocyclic compound, 956434-30-3, name is tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate, molecular formula is C13H17ClN2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
(step 1) To a solution of 1-cyclopentylethanol (0.22 mL) in toluene (4 mL) was added sodium hydride (0.14 g), and the resulting mixture was stirred at 100C for 15 min under a nitrogen atmosphere. A mixture of tert-butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.50 g), BINAP (0.033 g), Pd2(dba)3 (0.024 g) and toluene (4 mL) was added, and the resulting mixture was stirred at 100C for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0?40% ethyl acetate/hexane) to give tert-butyl 8-(l-cyclopentylethoxy)-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.45 g, 70%) as a white powder. 1H-NMR(CDCl3):delta1.27(3H,t,J=6.0Hz), 1.25-1.85(8H,m), 1.43(9H,s), 2.00-2.12(1H,m), 3.80-3.82(2H,m), 4.21(2H,brs), 4.33-4.45(2H,m), 5.01(1H,brs), 6.38(1H,d,J=8.1Hz), 7.30-7.50(1H,m)
The synthetic route of 956434-30-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2213675; (2010); A1;,
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