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CAS No. : | 257937-08-9 | MDL No. : | MFCD01860257 |
Formula : | C10H13BrN2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RPPLNTUECLIOOI-UHFFFAOYSA-N |
M.W : | 273.13 | Pubchem ID : | 10707388 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | tert-Butyl (3-bromopyridin-4-yl)carbamate (3f) (52%) was prepared from pyridine 2f (2.70 g, 13.9 mmol) [34]. White solid; mp 91-92 C. 1H NMR (400 MHz, CDCl3) delta 8.58 (s, 1H), 8.37 (d, J=5.6 Hz, 1H), 8.15 (d, J=5.6 Hz, 1H), 7.18 (s, 1H), 1.55 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 151.6, 151.4, 149.4, 143.1, 113.1, 109.6, 82.4, 28.1 (3C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 48h; | tert-Butyl 3-bromopyridin-4-ylcarbamate To a solution of 4-amino-3-bromopyridine (1.0 g, 5.78 mmol) in THF (10 mL), DIPEA (1.1 mL, 6.36 mmol) and (Boc)20 (1.39 g, 6.36 mmol) were added. The reaction mixture was stirred at rt. for two days. It was then quenched with 1N HCl solution and extracted with ethyl acetate (2*50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated to give tert-butyl 3-bromopyridin-4-ylcarbamate as a yellowish thick oil, (1.1 g, 70% yield). MS m/z 273,275(MH+); 1H NMR (300 MHz, CDCl3)delta ppm 1.51 (s, 9 H) 7.14 (s, 1 H) 8.12 (d, J=5.49 Hz, 1 H) 8.34 (d, J=5.86 Hz, 1 H) 8.55 (s, 1 H). |
37 g | With triethylamine; In tetrahydrofuran; for 2h; | To stirred a solution of 4-amino 3-bromo pyridine (10.0 g, 57.803 mmol) in THF (500 ml) were added triethylamine (8.8 g, 86.705 mmol) and Boc anhydride (37.89 g, 173.410 mmol). The reaction mixture was stirred for 2 h, before pouring into water (700 ml) and extracted with EtOAc (500 ml x 2), yielding ie/f-butyl (3- bromopyridin-4-yl)carbamate (37.0 g, 136.029 mmol). MS: 274.95 (M+2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; | Methyl 2-(4-(tert-butoxycarbonyl)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate To a mixture of methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate (383 mg, 1.0 mmol), <strong>[257937-08-9]tert-butyl 3-bromopyridin-4-ylcarbamate</strong> (328 mg, 1.2 mmol) and LiCl (84.8 mg, 2.0 mmol), in ethanol (3 mL) and toluene (3 mL) was added, 2M aqueous Na2CO3 (1.25 mL, 2.5 mmol) solution. The mixture was then degassed by the application of vacuum followed by flushing with N2.Pd(PPh3)4 (58 mg, 0.05 mmol) was then added and the reaction was heated at 80 C. overnight. The resultant mixture was then filtered and concentrated under vacuum, and the product residue was purified by Prep. reverse phase HPLC to afford the title compound as an off-white solid, (170 mg, 38% yield). MS m/z 450(MH+); 1H NMR (300 MHz, CDCl3) delta ppm 1.15-1.33 (m, 13 H) 1.63-1.98 (m, 6 H) 2.45 (m, 1 H) 3.92 (s, 3 H) 6.94 (s, 1 H) 7.75-7.89 (m, 2 H) 8.17 (s, 1 H) 8.21 (d, J=5.86 Hz, 1 H) 8.37 (s, 1 H) 8.45 (d, J=5.86 Hz, 1 H) 9.45 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium hydride; In N,N-dimethyl-formamide; | tert-Butyl (3-bromopyridin-4-yl)(prop-2-yn-1-yl)carbamate (4f) (69%) was prepared by alkylation of carbamate 3f (1.90 g, 6.95 mmol) with propargyl bromide [34] . It was obtained as a brown oil after chromatography on SiO2 (eluent, 1:1 petroleum ether/diethyl ether). 1H NMR (400 MHz, CDCl3) delta 8.80 (s, 1H), 8.55 (d, J = 5.1 Hz, 1H), 7.36 (bs, 1H), 4.71 (bs, 1H), 4.08 (bs, 1H), 2.25 (s, 1H), 1.43 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 153.2, 152.6, 149.5, 147.8, 125.2, 121.7, 82.3, 78.5, 73.1, 37.8, 28.2 (3C). |
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