Alternatived Products of [ 73387-60-7 ]
Product Details of [ 73387-60-7 ]
CAS No. : | 73387-60-7 |
MDL No. : | MFCD00121187 |
Formula : |
C11H12BrNO
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | IGZLESKZUATMSD-BQYQJAHWSA-N |
M.W : |
254.12
|
Pubchem ID : | 5376915 |
Synonyms : |
|
Application In Synthesis of [ 73387-60-7 ]
* 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.
- Upstream synthesis route of [ 73387-60-7 ]
- Downstream synthetic route of [ 73387-60-7 ]
- 1
-
[ 73387-60-7 ]
-
[ 49602-97-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 1.) Phosphorus oxychloride, 2.) Sodium perchlorate monohydrate / 1.) anhydr. Dichloromethane, room temp., 20 min; 0 deg C, 10 min, 2.) Dichloromethane/water, 0 deg C, 20 min
2: 73 percent / Sodium sulfide nonahydrate / dimethylformamide; H2O / 2 h / Ambient temperature
3: 61 percent / Pyridine, Hydroxylamine-O-sulfonic acid / ethanol; methanol / 0.5 h / Ambient temperature |
|
- 2
-
[ 73387-60-7 ]
-
[ 7064-31-5 ]
-
[ 13484-04-3 ]
- 3
-
[ 73387-60-7 ]
-
[ 60-34-4 ]
-
[ 73387-52-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
In N,N-dimethyl-formamide; at 20 - 75℃; for 5h;Product distribution / selectivity; |
Step 3: Preparation of 5-(4-bromophenyl)-1-methyl-1H-pyrazole; Alternative 1; A N,N'-dimethylformamide (15 mL) solution of 4-bromoacetophenone (10.60 g, 53.25 mmols) and N,N'-dimethylformamide dimethyl acetal (2.5 equivalents) was heated at 125 degrees Celcius for 3 hours. The dark red solution was cooled to room temperature. The volatiles were removed by rotary evaporation providing a red viscous oil. To this substance was added anhydrous N,N'-dimethylformamide (15 mL) and methyl hydrazine (7.6 g, 160 mmols, 3 equivalents). The mixture was stirred at room temperature for 1 hour and then heated at 75 degrees Celcius for 4 hours. The volatiles were removed by rotary evaporation and the crude residue was taken up in a small volume of methylene chloride. This red solution was applied to a cartridge of silica gel. The cartridge was eluted with a 20:80 mixture of ethyl acetate and hexanes, respectively. The appropriate fractions were combined and concentrated to produce 12.5 g of a white solid.1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.87-3.95 (m, J=2.22 Hz, 3H) 6.29-6.36 (m, 1H) 7.31 (dd, J=8.36 Hz, 2H) 7.52-7.56 (m, 1H) 7.62 (dd, J=2.05 Hz, 2H). |
|
In tert-butyl methyl ether; N,N-dimethyl-formamide; at 25℃;Product distribution / selectivity; |
Step 3: Preparation of 5-(4-bromophenyl)-1-methyl-1H-pyrazole; Alternative 2; 4-bromoacetophenone (20.0 g; 0.10 mole) and N,N-dimethylformamide dimethylacetal (28.5 mL; 0.20 mole) were mixed together in DMF (12 mL) and heated to 110 C. for 4 hours. The methanol and water that were generated during the reaction were distilled (6.2 mL). The mixture was cooled to 25 C. Methyl t-butyl ether (100 mL) and methylhydrazine (21.2 mL; 0.40 moles) were added and the mixture was stirred over night. The reaction mixture was washed with 1 M aqueous ammonium chloride (3×40 mL) and water (40 mL). The organic phase was dried by azeotropic distillation using a Dean-Stark apparatus. As an alternative to distillation, the solution was dried through an anhydrous magnesium sulfate cartridge. The solution was filtered through a silica gel cartridge (60 g). The product was flushed from the cartridge with methyl t-butyl ether. The fraction(s) containing product were combined and concentrated to about 70 mL by distillation. Heptane (120 mL) was added and distillation was continued until the pot temperature reached 98.4 C. About 100 mL of distillate was collected. The mixture was cooled to 40 C. The mixture was seeded and the temperature was maintained at 40 C. for 30 minutes while crystallization was initiated. The mixture was slowly chilled to 0 C. over 90 minutes. The mixture was held at 0 C. for 30 minutes. The mixture was filtered and the solid was washed (3×) with chilled (0 C.) heptane. The solid was dried on the filter. A cream-colored, crystalline solid (16.3 g; 68% yield) was obtained. The NMR data of the title compound are as per alternative 1. |
- 4
-
[ 73387-60-7 ]
-
[ 73387-46-9 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With hydrazine hydrate; In ethanol; for 3h;Reflux; |
General procedure: A mixture of enaminone(0.01 mol) and hydrazine hydrate 99% (0.01 mol) wasreAuxed in absolute alcohol for 3 hours. +e mixture waspoured into cold water. +e precipitate was obtained. +eproduct was obtained by 6ltration under vacuum. +eproduct was recrystallized from ethanol [25]. |
|
With hydrazine hydrate; In ethanol; at 80℃; for 1h; |
3-(4-bromophenyl)-l -H -pvrazoleStep B. A solution of (2E)-l-(4-bromophenyl)-3-(dimethylamino)prop~2-en-l-one (4.8 g, 18.9 mmol) and hydrazine monohydrate (2.78 mL, 56.7 mmol) in ethanol (40 mL) was heated at 8O0C for 1 h. Upon completion of the reaction as judge by TLC analysis, the solution was concentrated under vacuum. The residue was diluted with EtOAc (10OmL) and washed with water three times. The organic layer was dried with MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with EtOAc / Hexane to afford the title compound (3.8 g). LC/MS: m/e 223.06 (M+H). |
- 5
-
[ 73387-60-7 ]
-
[ 60-34-4 ]
-
[ 73387-52-7 ]
- 6
-
[ 57004-60-1 ]
-
[ 73387-60-7 ]
-
[ 1612217-68-1 ]
- 7
-
[ 64481-10-3 ]
-
[ 73387-60-7 ]
-
C27H14Br2Cl2O4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With indium(III) triflate In acetonitrile at 20℃; for 12h; regioselective reaction; |
|
- 8
-
[ 73387-60-7 ]
-
[ 17852-67-4 ]
-
5-(4-bromophenyl)-1-(4-methanesulfonyl-phenyl)-1H-pyrazole
[ No CAS ]
- 9
-
[ 24589-77-3 ]
-
[ 73387-60-7 ]
-
4-[5-(4-bromophenyl)pyrazol-1-yl]benzoic acid
[ No CAS ]
- 10
-
[ 73387-60-7 ]
-
[ 956268-33-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: silver tetrafluoroborate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide / 12 h / 80 °C / Inert atmosphere; Sealed tube
2: trimethylsilyl trifluoromethanesulfonate; N-Methyldicyclohexylamine / dichloromethane / 2 h / 0 - 20 °C / Sealed tube; Inert atmosphere |
|
- 11
-
[ 64-17-5 ]
-
[ 73387-60-7 ]
-
[ 20201-26-7 ]
- 12
-
[ 1115-70-4 ]
-
[ 73387-60-7 ]
-
3-(4-(4-bromophenyl)pyrimidin-2-yl)-1,1-dimethylguanidine
[ No CAS ]
- 13
-
[ 580-15-4 ]
-
[ 73387-60-7 ]
-
1-(4–bromophenyl)-3-(quinolin-6-ylamino)prop-2-en-1-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
92% |
With potassium hydrogensulfate; In ethanol; water; at 20℃; for 0.166667h;Sonication; |
General procedure: To a mixture of 3-aminoquinoline (1 mmol) and enaminones4a (1 mmol) in 6 cm3of EtOH: H2O(1:1) taken in a roundbottomflask was added KHSO4(2 mmol) and the resultingmixture was irradiated in an ultrasound cleaner for 10 minat room temperature when a solid product precipitated out.The progress and completion of the reaction was monitoredby TLC. The precipitate was collected by filtration withrepeated washing with water to ensure complete removal ofthe acid and then dried to give a practically pure 5a in 89%yield. Further purification of 5a was carried out by silicagel column chromatography using 50% EtOAc-hexane.The rest of the enaminones 5b-5e, 6a-6e, and 7a-7e wereequally easily prepared in 10-12 min in 79-94% overallyields. The structures of these enaminones were unambiguouslyassigned with the help of analytical and spectral datapresented hereunder. |