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With N-ethyl-N,N-diisopropylamine; In ethanol; at 100℃; for 16h;
A mixture of 2-bromo-6-fluoropyridine (500 mg, 2.8 mmol), tert-butyl 1,4-diazepane-1-carboxylate (568 mg, 2.8 mmol) in DIPEA (1.83 g, 14.2 mmol) in ethanol (10 mL) was heated at 100 C for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (100 mL). The solution was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford tert-butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate as a colorless oil (500 mg, 50%). MS (ESI) m/z: 356 [M+H] +.
tert-butyl 4-(3-nitro-5-(trifluoromethyl)phenyl)-1,4-diazepane-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85 mg
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In 1,4-dioxane; at 45℃; for 4h;
General procedure: To a solution of di-tert-butyl (3-bromo-5-(trifluoromethyl)phenyl)imidodicarbonate (step 1 intermediate) (2.2 g, 4.89 mmol) in 1,4-dioxane (20 mL) were added N,N,N?25 trimethylethylenediamine (636 jiL, 4.89 mmol), sodium tert-butoxide (1.40 g, 14.7 mmol),tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (447 mg, 0.49 mmol) and (2- biphenyl)di-tert-butylphosphinetriethylamine (JohnPhos) (37 mg, 1 .47mmol) at RT and the reaction mixture was stirred at 45 C for 4 h. The mixture was cooled to RT and filteredthrough celite. The filtrate was concentrated and the residue was dissolved in ethyl acetate. The organic solution was washed with 0.1 N HC1 followed by water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue obtained was purified by silica gel column chromatography to yield 2.01 g of the desired compound. The compound was as suchcarried forward to the next step without characterization.
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