CAS No. : | 791626-58-9 | MDL No. : | MFCD06738670 |
Formula : | C9H7BrN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GSKICCPQEZRQEC-UHFFFAOYSA-N |
M.W : | 223.07 | Pubchem ID : | 11183666 |
Synonyms : |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-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 |
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58% | With acetamide; potassium carbonate; at 200℃; for 2h; | Part D. Preparation of 6-bromo-2-aminoquinoline.; [00797] The product from Part C (173mg, 0.713mmol), acetamide (843mg, 14.27mmol) and potassium carbonate (493mg, 3.57mmol) were combined and heated at 200 0C for 2h. Cooled to room temperature, whereupon it solidified. Dissolved in a mixture of CHCl3 and water. Aqueous layer was extracted twice more with CHCI3, extracts were combined, washed with brine, dried over Na2SOφ filtered and concentrated under vacuum. Purification by silica gel column chromatography eluting with MeOH/CHCl3 gave title compound (92mg, 58 %). |
58% | [00539] Part D. Preparation of 6-bromo-2-aminoquinoline.; [00540] The product from Part C (173mg, 0.713mmol), acetamide (843mg, 14.27mmol) and potassium carbonate (493mg, 3.57mmol) were combined and heated at 200 0C for 2h. Cooled to room temperature, whereupon it solidified. Dissolved in a mixture of CHCI3 and water. Aqueous layer was extracted twice more with CHCI3, extracts were combined, washed with brine, dried over Na2SOφ filtered and concentrated under vacuum. Purification by silica gel column chromatography eluting with MeOH/CHCl3 gave title compound (92mg, 58 %). | |
34% | With acetamide; potassium carbonate; at 200℃; for 2h; | A mixture of 6-bromo-2-chloro-quinoline (2.0 g, 8.3 mmol), acetamide (9.74 g, 165 mmol) and potassium carbonate (3.4 g, 25 mmol) was heated at 200 C for 2 h. The reaction mixture was allowed to cool to rt whereupon the mixture solidified. The residue was taken up in DCM (15 ml_) and water (10 ml_), and the layers separated. The aqueous layer was extracted with DCM (2 x 15 ml_), the combined organic extracts were washed with brine, dried (MgSCU) and concentrated under vacuum to yield the title compound as a beige solid (780 mg, 34 %).1H NMR dH(400 MHz, Chloroform-d) 8.01 (d, J = 8.6 Hz, 1 H), 7.83 - 7.78 (m, 1 H), 7.78 - 7.73 (m, 1 H), 7.61 (dd, J = 8.9, 2.2 Hz, 1 H), 7.51 (d, J = 8.9 Hz, 1 H), 4.94 (s, 2H); LCMS (Method B): 1.10 min, (222.9/224.9, MH+). |
Yield | Reaction Conditions | Operation in experiment |
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Step 2: 7-Bromo-[1,2,4]triazolo[1,5-a]quinoline (8b) 8a (497 mg, 2.46 mmol) and dimethoxymethyldimethylamine (1 mL) were combined in DMF (5 mL) and heated to 130 C. for 1 hour. The reaction was concentrated and redissolved in MeOH (5 mL) and pyridine (400 mg). Hydroxylamine-O-sulfonic acid (282 mg, 2.49 mmol) was added, and the mixture was stirred at room temperature for 3 days. The solution was concentrated and poured into water, and the resulting solid was filtered and dried to give the desired product, 8b. |
Yield | Reaction Conditions | Operation in experiment |
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78% | With trifluoroacetic acid; at 80℃; | A mixture of B80-1 (100 mg, 0.29 mmol) in TFA (4 mL) was stirred at 80 C overnight. After cooling to room temperature, the mixture was evaporated. The residue was dissolved in iN HC1 (10 mL) and washed with ethyl acetate (10 mL * 3). It was adjusted pH to 9 by iN NaOH and extracted with dichloromethane (20 mL * 3). The organic layer was dried over Na2504, filtered and concentrated to give the title compound as a yellow oil (50 mg, 78 %). |
With trifluoroacetic acid; for 1h;Heating / reflux; | Step 1: 6-Bromo-quinolin-2-ylamine (8a) 6-Bromo-2-chloro-quinoline (3.34 g, 13.8 mmol) was dissolved in p-methoxybenzylamine (5 mL) and heated to 140 C. for 1 hour. The mixture was cooled to room temperature, filtered, and concentrated. The residue was purified by silica gel chromatography, and the isolated material was refluxed in TFA (6 mL) for 1 hour. The mixture was concentrated and purified by silica gel chromatography to give the desired product, 8a. |
Yield | Reaction Conditions | Operation in experiment |
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61% | With triethylamine; In dichloromethane; at 20℃; for 17h; | Part E. Preparation of N-(6-bromoquinolin-2-yl)-N-(methylsulfonyl)methanesulfonamide.; [00799] Combined the product from Part D (90mg, 0.403 mmol) and CH2Cl2 (2.0ml) and added triethylamine (0.062ml, 0.444mmol) and methanesulfonyl chloride (0.035ml, 0.444mmol). Stirred at room temperature 16h. Added triethylamine (0.062ml, 0.444mmol) and methanesulfonyl chloride (0.035ml, 0.444mmol) and stirred at room temperature for Ih. Diluted with EtOAc, washed with 10% citric acid, 10% NaHCO3 and brine. Dried over Na2SO4, filtered and concentrated under vacuum. Dissolved in EtOAc and poured into excess hexane. Solid collected by filtration to give the title compound (94mg, 61%). |
61% | With triethylamine; In dichloromethane; at 20℃; for 17h; | [00541] Part E. Preparation of N-(6-bromoquinolin-2-yl)-N-(methylsulfonyl)methanesulfonamide.; [00542] Combined the product from Part D (90mg, 0.403mmol) and CH2Cl2 (2.0ml) and added triethylamine (0.062ml, 0.444mmol) and methanesulfonyl chloride (0.035ml, 0.444mmol). Stirred at room temperature 16h. Added triethylamine (0.062ml, 0.444mmol) and methanesulfonyl chloride (0.035ml, 0.444mmol) and stirred at room temperature for Ih. Diluted with EtOAc, washed with 10% citric acid, 10% NaHCO3 and brine. Dried over Na2SO4, filtered and concentrated under vacuum. Dissolved in EtOAc and poured into excess hexane. Solid collected by filtration to give the title compound (94mg, 61%). |
Yield | Reaction Conditions | Operation in experiment |
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63.1% | dmap; at 45 - 100℃; | (3) N-(6-bromoquinolin-2-yl)acetamide.; A pyrex reaction tube was charged with <strong>[791626-58-9]6-bromoquinolin-2-amine</strong> (200 mg, 897 μmol) and acetic anhydride (1692 μl, 17932 μmol). The tube was sealed and the mixture was heated at 45 0C. After 3 h, LCMS showed no conversion. Catalytic DMAP was added, and heating was continued for 2 h. Trace conversion was observed. The temperature was increased to 100 0C and the reaction was stirred overnight. LCMS showed complete conversion in the morning. The mixture was cooled to 0 0C and the solids were filtered and rinsed with ether to provide N-(6-bromoquinolin-2-yl)acetamide (150 mg, 63.1% yield) as a brown solid. MS (ESI pos. ion) m/z calc'd for CnH9BrN2O: 265.1/267.1; found 264.9/267.0. |
Yield | Reaction Conditions | Operation in experiment |
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12% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; at 90℃; for 2h; | EXAMPLE 46; N-(5-(2-amino-6-quinolinyl)-2-chloro-3-pyridinyl)-4- methoxybenzenesulfonamide; A reaction tube was charged with sodium carbonate (353 μl, 706 μmol), Pd(Ph3P)4 (16 mg, 14 μmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (100 mg, 235 μmol), <strong>[791626-58-9]6-bromoquinolin-2-amine</strong> (53 mg, 235 μmol) and 1.2 mL EtOH. The tube was sealed and the mixture was heated at 90 0C for 2 h. The mixture was diluted with CH2Cl2 and washed with water. The organic portion was dried with MgSO4, filtered and concentrated. The crude material was dissolved in MeOH/DMSO and purified by reverse phase chromatography, 10-90% ACN/0.1% TFA in water over 15 min. The aqueous portion was brought to ~pH 7 and extracted. The organic portion was dried, filtered and concentrated to provide N-(5-(2-aminoquinolin-6-yl)-2-chloropyridin-3-yl)-4- methoxybenzenesulfonamide (12 mg, 12% yield) as a light yellow solid. MS (ESI pos. ion) m/z calc'd for C2IH17ClN4O3S: 440.9/442.9; found 441.0/443.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.88 (s, 3 H), 6.88 (br s, 2 H), 6.89 (d, 1 H, J = 8), 7.15-7.18 (m, 2 H), 7.61 (d, 1 H, J = 8), 7.75-7.80 (m, 3 H), 7.97-8.00 (m, 2 H), 8.03-8.06 (m, 1 H), 8.62-8.63 (m, 1 H), 10.46 (br, s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
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With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In butan-1-ol; at 55℃;Inert atmosphere; | Step 1 : To a solution of <strong>[791626-58-9]6-bromoquinolin-2-amine</strong> (5.0 g, 22 mmol), o-tolylboronic acid (4.3 g, 31 mmol), saturated sodium carbonate (2.5 ml, 22 mmol) and «BuOH (50 ml, 546 mmol) under N2 was added dichlorobis (triphenyl-phosphine)palladium (II) (1.6 g, 2.2 mmol). The reaction mixture was heated to 55 C and allowed to stir overnight. The reaction mixture was allowed to cool to RT then was extracted with EtOAc and washed with water and brine (3 x) then dried over MgS0 and concentrated in vacuo to remove solvent. The crude orange solid was dissolved in DCM and loaded onto achromatography column and eluted with 0-75% EtOAc/Hexane then 100% EtOAc to give 6-o-tolylquinolin-2-amine as light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate;PS-PPh3-Pd; In 1,2-dimethoxyethane; ethanol; at 140℃; for 0.166667h;microwave irradiation; | Step 1; A mixture of l//-indol-6-ylboronic acid (43 mg, 0.27 mmol), 6-bromoquinolin-2 -amine (40 mg, 0.22 mmol), K2C03 (3M, 100 uL), PS-PPh3-Pd (20 mg, 0.11 mmol/g), andDME/EtOH (50%, 1 mL) was heated in a microwave at 140 C for 10 min. The resulting slurry was filtered and purified by HPLC (10-60% CH3CN/water modified with 0.1% TFA) to give 6-(l//-indol-6-yl)quinolin-2-amine (31 mg). MS (ESI, pos. ion) m/z: 260 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate;bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; In ethanol; water; at 85℃; for 8h;microwave irradiation; | Step 1; To a microwave reaction vessel was added ethyl-2-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoate (3.7 g, 13 mmol), <strong>[791626-58-9]6-bromoquinolin-2-amine</strong> (2.0 g, 9.0 mmol), PdCl2(PPh(t-Bu)2)2 (0.084 g, 0.13 mmol), potassium acetate (1.8 g, 18 mmol), EtOH (9.9 ml, 170 mmol) and water (2.4 ml, 134 mmol). The reaction mixture was heated at 85 C for 8 h, and was then partitioned between EtOAc and water. The organic layer was washed with water and brine and allowed to stand for 72 h. The supernatant was decanted from the resulting precipitate and the precipitate was dried in vacuo to give ethyl 2-(2-aminoquinolin-6-yl)benzoate. |
Yield | Reaction Conditions | Operation in experiment |
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64% | General Procedure VII-AETo a solution of compound I-If (0.3 g 1.34 mmol) and HATU (0.56 g 1.34 mmol) in dry DMF (15 mL) was added DMA (0.35 g, 2.68 mmol). The mixture was stirred for 1 h at room temperature. Then <strong>[791626-58-9]6-bromoquinolin-2-amine</strong> (VII-VIIIf, 0.288 g, 1.34 mmol) was added into the mixture. The reaction mixture was stirred overnight at room temperature, and quenched with saturate NH4Cl solution then extracted with EA (4×30 mL). Combined organic layer extracts was dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by chromatography on silica gel column to give compound VII-VIIIg (200 mg, yield: 64%). 1H NMR (300 MHz, DMSO-d6): δ8.45-8.45 (d, 1H), 8.44-8.44 (d, 1H), 8.33-8.29 (q, 1H), 7.32-7.28 (q, 2H), 4.06-4.04 (t, 1H), 3.34-3.30 (t, 2H), 1.83-1.69 (m, 4H), 1.43-1.28 (s, 9H), MS (ESI) m/z (M+Na)+ 443.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78.3% | To a round bottom flask was charged 2 (2.24g, 10.0mmol, 1.0equiv), 40mL trifluorotoluene and 20mL chloroform under N2. After compound 2 was dissolved, the mixture was cooled to 0-10C with an ice-bath. T-butylamine (5.3mL, 50.0mmol, 5.0equiv) was added followed by Ts2O (6.50g, 20.0mmol, 2.0equiv) while the temperature was kept at 5-12C. If the reaction were not completed within 30min, portions of t-butylamine (0.6equiv. to 4.0equiv.) and Ts2O (0.3equiv. to 2.3equiv.) would be charged until the reaction completed. The reaction was then treated with TFA 25mL at 70C for 10h. Most of the solvents could be removed under vacuum. The oil residue was diluted with CH2Cl2 and quenched with 50% aq solution NaOH to pH 9-10. The aqueous layer was extracted with CH2Cl2 (50mL) three times. The combined organic layers were dried with MgSO4. The solvent was removed by reduced pressure and the crude product was then purified by silica gel column chromatography (2% MeOH/CH2Cl2) to give the desired 4 as a gray solid (1.75g, 78.3% yield), m.p. 139-145C (lit [16]. 141-146C). 1H NMR (400MHz, CDCl3) δ (ppm): 7.79 (d, J=8.8Hz, 1H), 7.76 (d, J=2.2Hz, 1H), 7.61 (dd, J1=8.9Hz, J2=2.2Hz, 1H), 7.52 (d, J=8.9Hz, 1H), 6.73 (d, J=8.8Hz, 1H), 4.83 (s, 2H). |
[ 1170935-81-5 ]
6-Bromoquinolin-2-amine hydrochloride
Similarity: 0.97
[ 1170935-81-5 ]
6-Bromoquinolin-2-amine hydrochloride
Similarity: 0.97
[ 1170935-81-5 ]
6-Bromoquinolin-2-amine hydrochloride
Similarity: 0.97