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CAS No. : | 1194688-12-4 | MDL No. : | MFCD13190583 |
Formula : | C12H11BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 263.13 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
66% | With sodium t-butanolate In toluene at 80℃; for 16h; | 25.25A Example 25; N-benzyl-5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridin-3-amine; Example 25A; N-benzyl-5-bromopyridin-3-amine; 3,5-Dibromopyridine (20.0 g, 84.4 mmol) and benzylamine (9.23 mL, 84.4 mmol) were dissolved in toluene (100 mL). Pd2(dba)3 (1.55 g, 1.69 mmol), BINAP (2.10 g, 3.38 mmol) and sodium tert-butoxide (12.2 g, 127 mmol) were added to the reaction mixture. The reaction was heated to 80° C. for 16 h, then allowed to cool to ambient temperature, diluted with ether (400 mL) and washed with brine (3×100 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (25% EtOAc in hexanes) to afford the title compound as a slightly yellow solid (14.75 g, 66%). MS (DCI/NH3) m/z 263 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90℃; for 18h; | Example 25B; (3aR,6aS)-tert-butyl 5-(5-(benzylamino)pyridin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate; The product from Example 25A (201.7 mg, 0.77 mmol) was dissolved in tolulene (7.7 mL). To the reaction mixture was added the product from Example 1C (204.6 mg, 0.96 mmol), Pd2(dba)3 (27.0 mg, 0.029 mmol), BINAP (60.7 mg, 0.097 mg) and sodium tert-butoxide (105.3 mg, 1.10 mmol). The reaction was heated to 90 C. overnight (18 h), then allowed to cool to ambient temperature, diluted with water (100 mL) and extracted with CH2Cl2 (3×50 mL). The organic extracts were combined and washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative HPLC on a Waters Nova-PakHR C18 6 mum 60 Prep-Pak cartridge column (40 mm×100 mm) using a gradient of 10% to 100% acetonitrile in 10 mM aqueous ammonium acetate over 12 min at a flow rate of 70 mL/min to provide the title compound MS (DCI/NH3) m/z 395 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In N,N-dimethyl-formamide; acetonitrile at 160℃; for 0.25h; Inert atmosphere; Microwave irradiation; | 2 6-(5-(Benzylamino)pyridin-3-yl)-1H-benzo[d]imidazol-2-amine (compound 16c) General procedure: [0193] To a solution of compound 15b (39 mg, 0.15 mmol), compound 6a (39.7 mg, 0.15 mmol) and Pd(PPh3)4 (17.4 mg, 0.02 mmol) in anhydrous MeCN (1 mL) and anhydrous DMF (1 mL) was added 1 M Na2CO3 (0.32 mL, 0.32 mmol) under nitrogen. The resulting mixture was irradiated in microwave at 160°C for 15 min. After being quenched with water (5 mL), the aqueous layer was extracted with EtOAc (2 10 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was and purified by column chromatography on silica gel (MeOH/CH2Cl2, 5:95 to 10:90) to give compound 16c (21.1 mg, 44.3%) as a brown solid; 1H NMR (DMSO-d6, 500 MHz) 10.75 (1H, br), 7.98 (1H, d, J = 1.5 Hz), 7.88 (1H, d, J = 2.5 Hz), 7.39 (2 H, d, J = 7.6 Hz), 7.33 (2 H, t, J = 7.6 Hz), 7.25-7.21 (2 H, m), 7.13-7.12 (1H, d, J = 8.1Hz), 7.06-7.05 (2 H, m), 6.50 (1H, t, J = 5.6 Hz), 6.20 (2 H, br), 4.36 (2 H, d, J = 5.6 Hz); HRMS (ESI-TOF) m/z: [M + H]+ calculated for C19H18N5 316.1557; found 316.1560. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In N,N-dimethyl-formamide; acetonitrile at 160℃; for 0.25h; Inert atmosphere; Microwave irradiation; | 2 N-Benzyl-5-(imidazo[1,2-a]pyridin-6-yl)pyridin-3-amine (compound 16a) General procedure: [0191] To a solution of compound 15a (35 mg, 0.13 mmol), compound 6a (43 mg, 0.27 mmol) and Pd(PPh3)4 (15 mg, 0.01 mmol) in anhydrous MeCN (1 mL) and anhydrous DMF (1 mL) was added 1 M Na2CO3 (0.27 mL, 0.27 mmol) under nitrogen. The resulting mixture was irradiated in microwave at 160°C for 15 min. After being quenched with water (5 mL), the aqueous layer was extracted with EtOAc (2 10 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was and purified by column chromatography on silica gel (MeOH/CH2Cl2, 5:95 to 10:90) to give compound 16a (10.7 mg, 27%) as a light brown solid; 1H NMR (CDCl3, 500 MHz) 8.26 (1H, s), 8.17 (1H, s), 8.10 (1H, s), 7.67-7.64 (3 H, m), 7.39-7.31 (6 H, m), 7.00 (1H, s), 4.42 (2 H, d, J = 3.0 Hz), 4.30 (1H, br); HRMS (ESI-TOF) m/z: [M + H]+ calculated for C19H17N4 301.1448; found 301.1454. |