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Structure of 1458-98-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1458-98-6 |
Formula : | C4H7Br |
M.W : | 135.00 |
SMILES Code : | C=C(C)CBr |
MDL No. : | MFCD00134155 |
InChI Key : | USEGQJLHQSTGHW-UHFFFAOYSA-N |
Pubchem ID : | 357785 |
GHS Pictogram: |
![]() ![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H225-H302-H314-H411 |
Precautionary Statements: | P210-P280-P305+P351+P338-P310 |
Class: | 3(8) |
UN#: | 2924 |
Packing Group: | Ⅱ |
* 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 |
---|---|---|
With potassium carbonate; In acetone; for 24h;Reflux; | General procedure: General procedure: To a solution of 8-hydroxyquinoline 4 (7 mmol) and (2-methyl)allyl bromide (10.5 mmol, 1.5 equiv) in acetone (30 mL) was added potassium carbonate (21 mmol, 3 equiv). After stirring for 24 h at reflux temperature, the reaction mixture was poured into water (15 mL) and extracted with dichloromethane (3 × 15 mL). The combined organic extracts were dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent in vacuo afforded the crude products 5a-n, which were purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetone; for 24h;Reflux; | General procedure: General procedure: To a solution of 8-hydroxyquinoline 4 (7 mmol) and (2-methyl)allyl bromide (10.5 mmol, 1.5 equiv) in acetone (30 mL) was added potassium carbonate (21 mmol, 3 equiv). After stirring for 24 h at reflux temperature, the reaction mixture was poured into water (15 mL) and extracted with dichloromethane (3 × 15 mL). The combined organic extracts were dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent in vacuo afforded the crude products 5a-n, which were purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | General procedure: KOt-Bu (4.56 g, 40.73 mmol) was added to a stirred solution of2-chloro-5-iodopyridin-4-ylamine (8.62 g, 33.94 mmol) inanhydrous THF (140 mL), and the mixture was stirred at r.t. for15 min. 3-Bromo-2-methylpropene (5.51 g, 40.73 mmol) wasadded, and the mixture was stirred at r.t. overnight. The solventwas removed in vacuo and the residues partitioned betweenCH2Cl2 (100 mL) and H2O (100 mL). The organic layer was separated,the solvent removed in vacuo, and the residues subjectedto column chromatography on silica. Elution with 5-20% EtOAcin PE afforded (2-chloro-5-iodopyridin-4-yl)-(2-methylallyl)amine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In acetone;Reflux; | [00306j To a solution of <strong>[52427-05-1]2-bromo-5-nitro-phenol</strong> (0.5 g, 2.3 mmol) in acetone (20 mL) was added 3-bromo-2-methyl-propene (465 mg, 3.4 mmol) and K2C03 (633 mg, 4.6 mmol), and the mixture was refluxed overnight. The reaction mixture was cooled to RT and the solvent was concentrated. The residue was dissolved in EA, washed with water, washed with brine. The organics were concentrated and purified by silica gel chromatography (EA: PE, 1:20) to give 0.5 g (80percent) of the title compound. [M+H] Calc?d for C,0H,0BrNO3, 271; Found, 271. |
63.25% | To a solution of 23.2 (0.76 g, 3.57 mmol, 1.0 eq) in acetone (8 mL) were added K2CO3 (1.20 g, 8.71 mmol, 2.5 eq) and NaI (0.575 g, 3.83 mmol, 1.1 eq) at room temperature and stirred for 20 minutes. To the mixture 3-Bromo-2-methylpropane (0.611 g, 4.53 mmol, 1.3 eq) was added and reaction was heated at reflux temperature for 2 hours. After completion of the reaction, mixture was diluted with water and extracted with EtOAc. Organic layer was dried over sodium sulphate and concentrate under reduced pressure at 45° C. Crude was purified by column chromatography to afford 23.3 (0.60 g, 63.25percent). MS (ES): m/z=273.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | To a stirred solution of methyl 2,5-dihydroxybenzoate(4 g, 23.8 mmol) in acetone (10 mL) potassium carbonate (3.2 g, 23.8 mmol) was added and stirred for 15 min.To this mixture methylallyl bromide (3.6 mL, 35.7 mmol) was added and stirred for 2.5 h. After the completion of the reaction, the mixture was concentrated under vacuum to remove excess acetone. The reaction mixture was then diluted with water and extracted with ethyl acetate (2 × 100 mL). The combined extracts were washed successively with water (50 mL), saturated aqueous solution of sodium thiosulfate (20 mL), brine (50mL), dried (anhydrous Na2SO4), filtered and concentrated under reduced pressure. Column chromatography ofthe residue afforded ester 15 as oil (4.5 gm, 87%). Rf (1:5 EA(ethyl acetate)/hexane) 0.75; 1H NMR (400 MHz,CDCl3): δ 10.38 (s, 1H), 7.31 (d, J 3.2 Hz, 1H), 7.11 (dd, J 3.2, 8.8 Hz, 1H), 6.91 (d, J 8.8 Hz, 1H), 5.09 (s, 1H), 4.99(s, 1H), 4.39 (s, 2H), 3.95 (s, 3H), 1.83 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 170.3, 156.1, 151.1, 140.8, 124.7,118.5, 113.3, 112.9, 11.9, 72.5, 52.4, 19.5; IR (KBr): ν 3220, 2954, 2362, 1683, 1488, 1218, 771 cm-1; HRMS(ESI): m/z calculated for C11H11O3: requires: 191.0708 for [M-OMe]+; found: 191.0706. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.3% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | (1)will6g (16.3mmol)Dehydrated icariinversusAfter mixing 80 mL of DMF, 3.38 g (24.5 mmol) of anhydrous potassium carbonate was added thereto.After stirring for 10 minutes, 1.97 mL (19.6 mmol) of 3-bromo-2-methylpropene was slowly added dropwise thereto.Plus,The reaction was carried out at room temperature.(2) TLC (petroleum ether: dichloromethane: methanol = 40:40:1) was followed for the reaction, and the reaction was completed after about 8 hours. After the reaction was completed, the reaction solution was poured into 500 mL of ice water, and the mixture was allowed to stand for one hour after stirring. A large amount of pale yellow solid was precipitated, suction filtered, and the filter cake was washed three times with water and then dried to obtain a crude product of YS-10. The crude product was passed through a silica gel column (petroleum ether: methylene chloride:methanol = 40:40:1) to afford YS-10 (6.4 g, yield 93.3%) |
88% | (11) Introduction of propylene group: After mixing 0.1 mol of product X with 500 ml of dimethylformamide, 0.15 mol of anhydrous potassium carbonate was added thereto, and after stirring for 10 minutes, a 0.12 mol-fold amount of slowly3-Bromo-2-methylpropene was added and allowed to react at room temperature. TLC (petroleum ether: dichloromethane: methanol = 40: 40: 1) followed the reaction, and the reaction was complete after about 8 hours. After the reaction was completed, the reaction solution was poured into 500 mL of ice water, and the mixture was allowed to stand for one hour after stirring. A large amount of light yellow solid precipitated, filtered with suction, the filter cake was washed with water three times, and dried to obtain a crude YS-10 product. The crude product was passed through a silica gel column (petroleum ether: dichloromethane: methanol = 40: 40: 1) to obtain the product XI, namely YS-10 (37 g, yield 88%). |
Tags: 1458-98-6 synthesis path| 1458-98-6 SDS| 1458-98-6 COA| 1458-98-6 purity| 1458-98-6 application| 1458-98-6 NMR| 1458-98-6 COA| 1458-98-6 structure
A225436 [15378-31-1]
3-Bromo-2-(bromomethyl)prop-1-ene
Similarity: 0.92
A225436 [15378-31-1]
3-Bromo-2-(bromomethyl)prop-1-ene
Similarity: 0.92
A225436 [15378-31-1]
3-Bromo-2-(bromomethyl)prop-1-ene
Similarity: 0.92
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