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CAS No. : | 3034-53-5 |
Formula : | C3H2BrNS |
M.W : | 164.02 |
SMILES Code : | BrC1=NC=CS1 |
MDL No. : | MFCD00005316 |
InChI Key : | RXNZFHIEDZEUQM-UHFFFAOYSA-N |
Pubchem ID : | 76430 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
57% | With n-butyllithium; carbon dioxide; | Example 105 ETHYL 2-[N-(1'-AMINOCITRACONAMIDO)]-4-(2'-THIAZOLYL)PYRIMIDINE-5-CARBOXYLATE 2-Bromothiazole (8.25 g, 0.05 moles) in anhydrous ether (60 mL) is added dropwise to a solution of nBuLi (34 mL, 1.5M solution, 0.051 mmol) in anhydrous ether (60 mL) cooled to -78° C. and stirred for 30 minutes. Carbon dioxide is bubbled into the solution and after saturation is achieved, the reaction mixture is poured over dry-ice. H2 O (10 mL) is added and the mixture basified to pH=9 with NaOH (1N). The aqueous layer is acidified with concentrated HCl to pH <3 then extracted into ether, dried (MgSO4) and concentrated to provide the thiazole-2-carboxylic acid in 57percent yield (3.2 g); 1 H NMR (MeOD) delta 8.00 (d, 1H); 7.94 (d, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 7 1-(4-Methyl-2-oxazolyl)-1-(2-thiazolyl)ethanol From 2-bromothiazole and <strong>[90892-97-0]2-acetyl-4-methyloxazole</strong> (J. Chem. Soc., Chem. Commun., 1984, 258). 13 C Nmr (CDCl3) 11.3, 27.9, 73.1, 119.9, 135.4, 136.4, 142.6, 164.6 and 174.1 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 160℃; for 0.0833333h;Microwave irradiation; | 6.21. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxy]-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
38% | With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 160℃; for 0.0833333h;Sealed tube; Microwave irradiation; | To a 40 ml microwave reactor was added 1.04 g of 2-formylphenylboronic acid (6.9 mmol) of 1.14 g of 2-bromothiazole(6.9 mmol), 240 mg of bistriphenyl-phosphine palladium dichloride (Pd (PPh3) 2Cl2, 0.34 mmol). then,To the mixture was added 13.8 ml of 1 M Na2CO3 (13.8 mmol) and 10 ml of CH3CN. Sealed reactor,The reaction was run under microwave at 160 C for 5 minutes.LCMS shows the desired reaction of the desired product. The reaction mixture was then poured into a separation funnel. Add 200 ml of dichloromethaneAlkane and 100 ml of water for extraction. The dichloromethane layer was dried over MgSO4. The solvent was removed to give the crude product, which was passed through siliconThe column chromatography was eluted with a hexane / ethyl acetate mixture (5/1 to 2/1)To give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; for 6h;Reflux; | Example 4 1-phenyl-8-[[2-(2-thiazolyl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one (Compound 24) Step A: To a mixture of 2-bromothiazole (826 mg, 4.99 mmol) and tetrakis(triphenylphosphine) palladium (0) (175 mg, 0.151 mmol) in 1,2-dimethoxyethane (20 mL) was added 2-formylbenzeneboronic acid (0.9017 g, 6.01 mmol) and 1 N aqueous NaHCO3 (8 mL). The resultant mixture was heated at reflux for 6 hrs. The reaction mixture was diluted with water and extracted with EtOAc (2 X 50 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The crude product was purified by gradient flash chromatography (10% to 25% EtOAc in hexane) to yield 2-(2-thiazolyl)benzaldehyde as a white solid. MS (loop pos) MH+ = 190.1 1 H NMR (300 MHz, CDCl3) 7.50 (m, 1 H), 7.55-7.60 (m, 1 H), 7.65-7.70 (m, 1 H), 7.75-7.80 (m, 1 H), 7.95-7.97 (m, 1 H), 8.00-8.05 (m, 1 H), 10.5 (s, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In dichloromethane; water; acetonitrile; | 6.54. Synthesis of (S)-2-Amino-3-(4-{2-amino-6-[2,2,2-trifluoro-1-(2-thiazol-2-yl-phenyl)-ethoxyl-pyrimidin-4-yl}-phenyl)-propionic acid To a 40 ml microwave reactor, was added 1.04 g of 2-formyl phenylboronic acid (6.9 mmoles), 1.14 g of 2-bromo thiazole (6.9 mmoles), 240 mg of palladium bistriphenyl-phosphine dichloride (Pd(PPh3)2Cl2, 0.34 mmoles). Then, 13.8 ml of 1M Na2CO3 (13.8 mmoles) and 10 ml of CH3CN were added to the mixture. The reactor was sealed, and the reaction was run under microwave at 160 C. for 5 minutes. LCMS shows completion of the reaction with desired product. The reaction mixture was then poured into a separation funnel. Then 200 ml of methylene chloride and 100 ml of water were added for extraction. The methylene chloride layer was dried over MgSO4. Removal of solvent gave a crude product, which was purified by silica gel column chromatography eluding with hexanes/ethyl acetate mixture (5/1 to 2/1) to give pure 2-thiazol-2-yl-benzaldehyde (0.5 g, yield: 38%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.9% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 2.5h;Microwave irradiation; | To a mixture of 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- benzonitrile (100 mg, 0.405 mmol), 2-bromothiazole (0.11 mL, 1.221 mmol), and K2CO3 (168 mg, 1.214 mmol) in 1,4-dioxane (1.5 mL) and water (0.5 mL) was added Pd(Ph3P)4 (5 mg, 0.004 mmol). The vial was capped and the reaction mixture was heated in a Biotage Initiator microwave reactor to 100 0C for 30 min followed by an additional 2 h at 100 0C. Water (4 mL) and EtOAc (5 mL) were added to the reaction mixture. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 3 mL). The combined organic layers were washed with brine (3 x 1 mL) and concentrated under a stream of nitrogen at 50 0C onto Isolute. Purification via flash column chromatography (0-20% EtOAc/hexanes) afforded the title compound (2.4 mg, 2.9%). LC-MS m/z 205 (M+H)+, 0.87 min (ret time). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | 2-(2-methyl-lH-indol-5-yl)thiazole[00319] To a slurry of zinc dust (1.21 g, 18.6 mmol) in tetrahydrofuran (5 mL) was added 1,2-dibromoethane (0.144 mL, 1.67 mmol). This slurry was heated to a rapid boil with a heat gun twice (to incite evolution of ethylene). To this resulting slurry was addedchlorotrimethylsilane (0.0950 mL, 0.743 mmol) followed by a solution of 2-bromothiazole (1.02 g, 6.19 mmol) in tetrahydrofuran (3 mL). The reaction was stirred for 15 minutes, after which a solution of Pd(Ph3P)4 (0.143 g, 0.124 mmol) and 5-bromo-2-methyl-lH-indole (1.30 g, 6.19 mmol) was added. The reaction was refluxed at 95 °C for 24 hours, after which the reaction was cooled to room temperature, filtered through a pad of celite, extracted with dichloromethane (3 x 50 mL), dried (sodium sulfate), filtered and concentrated to an orange residue. Purification of the reaction mixture by silica gel chromatography (Luknova 120g, 20 mL/min) using 10 to 50percent ethyl acetate in hexanes over 60 minutes afforded 2-(2-methyl-lH- indol-5-yl)thiazole (640 mg, 2.99 mmol, 48 percent yield) as a yellow foam. 1H NMR (400 MHz, CDCI3) 6 (ppm): 8.12 (s, 1H), 8.08 (br. s, 1H), 7.82 (d, 1H), 7.76 (dd, 1H), 7.31 (dd, 1H), 7.24 (d, 1H), 6.28 (s, 1H), 2.45 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | To a solution of 4-bromo-3-cyclopropyl-lH-pyrazole 25 (247 mg, 1.3 mmol) in dimethylformamide (DMF) (10 mL) was added NaH (120 mg, 5 mmol). The mixture was stirred for 0.5 h at room temperature and the 2-bromo-l,3-thiazole (328 mg, 2 mmol) was added. The reaction mixture was stirred for 1 h at room temperature. The reaction temperature was raised to 90C and stirred overnight. The reaction was quenched with MeOH and solvent was removed in vacuo. The residue was treated with water and EtOAc. The organic layer was separated and aqueous was extracted with EtOAc. The combined organic phase was dried over Na2SC>4, filtered, and concentrated to give crude product. The crude product was purified on ISCO columns. Fractions containing pure product were combined and evaporated to give 26 as a yellow solid (170 mg, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With hydrogenchloride; In ethanol; water; at 100℃; for 30h; | A solution of intermediate lb (1.50g, 9.37mmol) in EtOH (45ml) and water (5ml) was treated with 2-bromothiazole (1.69ml, 18.7mmol) and cone. HQ (1.61ml, 187mmol) and stirred at 100C for 6h. Aftre addition of further 2-bromothiazole (1.69ml, 18.7mmol) the solution was heated for a further 24h then cooled and taken to pH14 with aqueous NaOH solution. After extraction with 10% EtOH in DCM then DCM, the organics were dried (MgS04), filtered and evaporated. The residue was purified by column chromatography (Si02, 5% acetone in DCM) to afford intermediate IVb as a white solid (493mg, 22%). H NMR (300 MHz, DMSO-d6) δ 10.36 (s, 1H), 8.46 (s, 1H), 8.10 (t, J = 1.8 Hz, 1H), 7.63 (s, 1H), 7.56 (ddd, J = 8.1, 2.2, 1.1 Hz, 1H), 7.39 (t, J = 7.9 Hz, 1H), 7.33 - 7.29 (m, 2H), 6.95 (d, J= 3.7 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.00% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 12h;Inert atmosphere; | A mixture of 4-nitrophenyl)boronic acid (23.00 g, 137.78 mmol, 1.00 eq.), 2-bromothiazole (25.54 g, 155.69 mmol, 14.03 mL, 1.13 eq.), Na2C03 (36.51 g, 344.45 mmol, 2.50 eq.) and Pd(dppf)Cl2.CH2Cl2 (6.75 g, 8.27 mmol, 0.06 eq.) in Tol. (250.00 mL)/H20 (100.00 mL)/dioxane (250.00 mL) was degassed and purged with N2 for 3 times. The mixture was stirred at 80C for 12 hrs under N2 atmosphere and LCMS showed the reaction was complete. The mixture was concentrated and the residue was purified by column chromatography (Petroleum ethenEthyl acetate=50: l to 5: 1) to give 2-(4-nitrophenyl)thiazole (14.00 g, 67.89 mmol, 56.00% yield) as a yellow solid. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.35 - 8.29 (m, 2H), 8.21 - 8.12 (m, 2H), 7.99 (d, J = 3.2 Hz, 1H), 7.50 (d, J = 3.2 Hz, 1H). |
Tags: 2-Bromothiazole | Bromides | Thiazoles | Heterocyclic Building Blocks | Organic Building Blocks | 3034-53-5
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Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL