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CAS No. : | 1000578-18-6 | MDL No. : | MFCD09878133 |
Formula : | C9H10BrI | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YPAAYRSBEOPROG-UHFFFAOYSA-N |
M.W : | 324.98 | Pubchem ID : | 44891189 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 130℃; for 0.5h;Microwave irradiation; | A microwave vial was charged with 2-bromo-l-iodo-4-isopropylbenzene (Oakwood, 0.117 g, 0.359 mmol), N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4- dihydro-2H-benzo[b][l,4]oxazine-7-sulfonamide (INTERMEDIATE M, 0.150 g, 0.359 mmol), Xantphos (0.042 g, 0.072 mmol), Pd2(dba)3 (0.033 g, 0.036 mmol) and sodium tert-butoxide (0.069 g, 0.719 mmol). The mixture was diluted with toluene (3.59 ml), and purged with nitrogen, and stirred at 130 C in the microwave for 30 minutes, until clean conversion to the desired product. After completion, the reaction was filtered over a plug of Celite, washing well with DCM. The filtrate was concentrated in vacuo. The crude material was purified using a 5-g SCX column (product eluted with methanol wash to yield 4-(2-bromo- 4-isopropylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H- benzo[b][l,4]oxazine-7-sulfonamide (0.175 g, 0.285 mmol, 79 % yield) as an orange oil. m/z (ESI) 614.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.96 g | General procedure: The synthesis was carried out in two steps. The firststep was the diazotization reaction of 2-bromo-4-isopropylanilinefollowed by the treatment of theobtained diazo compound by potassium iodide. Asolution of 3.32 g of sodium nitrite in 17.5 mL of distilledwater was added over 30 min to a mixture of9.35 g of 2-bromo-4-isopropylaniline (43.67 mmol),26 mL of distilled water, and 12.66 mL of concentratedhydrochloric acid cooled down to 3C. Then 23 mL ofmethylene chloride was added, and the formed masswas stirred at 5C to the dissolution of the precipitate.The excess of nitrite was neutralized using carbamide,and then a solution of 10.87 g of potassium iodide in17.5 mL of distilled water was added dropwise to thesolution. The reaction mass was stirred for 16 h atroom temperature, and then the organic phase wasseparated. The aqueous phase was extracted withmethylene chloride. The organic fractions were combined,dried over anhydrous calcium chloride, andevaporated. The residue was dissolved in n-hexaneand passed through a layer of alumina. After the evaporationand distillation of the residue, 6.96 g of theproduct, 1-iodo-2-bromo-4-isopropylbenzene, was obtained.The second step was the cross-coupling of 1-iodo-2-bromo-4-isopropylbenzene and trimethylsilyldiphenylphosphine.4.125 g of 1-iodo-2-bromo-4-isopropylbenzene,3.365 g of trimethylsilyldiphenylphosphine,and 0.20 g of palladium phenyldibenzophospholcomplex (DBP)2Pd were dissolved in 25 mL oftoluene. The obtained solution was stirred at 70C inan argon flow for 24 h, cooled down to room temperature,and filtered through silica gel. The filtrate wasevaporated, and the residue was washed with diethylether. 3.9 g of 1-bromo-2-diphenylphosphino-5-isopropylbenzenewas obtained.Yield 80%. 1H NMR spectrum (300 MHz,CDCl3): δ (ppm) 7.44 (d, J = 3 Hz, 1H, Ar-H), 7.33-7.22 (m, 10H, Ar-H), 7.01 (d, J = 1 Hz, 1H, Ar-H),6.63 (dd, 1H, J = 3 Hz, J = 8 Hz, Ar-H), 2.84 (m, 1H,J = 7 Hz, CH), 1.20 (d, 6H, J = 7 Hz, CH3). 31P{1H}spectrum (121 MHz, CDCl3): δ (ppm) -5.88 (s,PPh2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 24h;Inert atmosphere; Schlenk technique; | General procedure: An oven-dried Schlenk tube was charged with a magneticstir bar, binucleophile 2-mercaptobenzimidazole 2 (1.0 mmol, 1.0 equiv), CuI(0.1 mmol, 10 mol %), phen (0.2 mmol, 20 mol %), and K2CO3 (2.0 mmol, 2equiv). The tube was capped and then evacuated and backfilled with nitrogen(3 times). Under a positive pressure of nitrogen, a solution of o-dihaloarene 1(1.05 mmol, 1.05 equiv) in DMF (3 mL) was added via syringe. The tube wassealed and allowed to stir at 120 C (monitored by TLC). After being cooled toroom temperature, EtOAc (40 mL) was added and the mixture was washedwith brine (20 mL 3). The organic phase was dried over Na2SO4 andconcentrated. The residue was purified by column chromatography on silicagel using petrol/EtOAc (10:1?3:1, v:v) as eluent to give product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 50℃; for 8h;Inert atmosphere; | General procedure: To a three-necked flask charged with a magnetic stirring bar was added 1-bromo-2-iodobenzene (15 mmol), ethynyltrimethylsilane (15 mmol), Pd(PPh3)2Cl2 (2 mol %), CuI (1 mol %) in triethylamine (50 mL) under nitrogen. The mixture wasstirred at 50 C for 8 hours. the solvent was removed by rotary evaporation. The residue was treated with water and extracted with dichloromethane. The combined organic layer was concentrated under reduced pressure. The crude product was purified flash column chromatography on silica gel using petroleum ether as an eluent.To a solution of trimethyl(phenylethynyl)silane (10 mmol) in methanol (15 mL) and THF (15 mL) was added K2CO3 (4 equiv.) and stirred at rt for 6 hours. The resulting mixture was treated with water and extracted with ethyl ether. The combined organic layer dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by silica gel column chromatography to afford the pure product 1a2 in 85 % yield. Substrates1b2 and 1c were also prepared following the general procedure A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With palladium phenyldibenzophosphol complex; In toluene; at 70℃; for 24h;Inert atmosphere; | General procedure: The synthesis was carried out in two steps. The firststep was the diazotization reaction of 2-bromo-4-isopropylanilinefollowed by the treatment of theobtained diazo compound by potassium iodide. Asolution of 3.32 g of sodium nitrite in 17.5 mL of distilledwater was added over 30 min to a mixture of9.35 g of 2-bromo-4-isopropylaniline (43.67 mmol),26 mL of distilled water, and 12.66 mL of concentratedhydrochloric acid cooled down to 3C. Then 23 mL ofmethylene chloride was added, and the formed masswas stirred at 5C to the dissolution of the precipitate.The excess of nitrite was neutralized using carbamide,and then a solution of 10.87 g of potassium iodide in17.5 mL of distilled water was added dropwise to thesolution. The reaction mass was stirred for 16 h atroom temperature, and then the organic phase wasseparated. The aqueous phase was extracted withmethylene chloride. The organic fractions were combined,dried over anhydrous calcium chloride, andevaporated. The residue was dissolved in n-hexaneand passed through a layer of alumina. After the evaporationand distillation of the residue, 6.96 g of theproduct, 1-iodo-2-bromo-4-isopropylbenzene, was obtained.The second step was the cross-coupling of 1-iodo-2-bromo-4-isopropylbenzene and trimethylsilyldiphenylphosphine.4.125 g of 1-iodo-2-bromo-4-isopropylbenzene,3.365 g of trimethylsilyldiphenylphosphine,and 0.20 g of palladium phenyldibenzophospholcomplex (DBP)2Pd were dissolved in 25 mL oftoluene. The obtained solution was stirred at 70C inan argon flow for 24 h, cooled down to room temperature,and filtered through silica gel. The filtrate wasevaporated, and the residue was washed with diethylether. 3.9 g of 1-bromo-2-diphenylphosphino-5-isopropylbenzenewas obtained. |
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