Structure of 914348-80-4
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 914348-80-4 |
Formula : | C10H6FNOS |
M.W : | 207.22 |
SMILES Code : | FC1=CC=C(C=C1)C2=NC=C(S2)C=O |
MDL No. : | MFCD05864658 |
InChI Key : | FPMAURQPBMLMSS-UHFFFAOYSA-N |
Pubchem ID : | 45036823 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
78% | In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 2h; | Step 2: -(2-(4-Fluorophenyl)thiazol-5-yl)ethanol To a solution of <strong>[914348-80-4]2-(4-fluorophenyl)thiazole-5-carbaldehyde</strong> (500 mg, 2.41 mmol) in THF (25 mL) was added 3M methyl magnesium bromide in ether (1.61 mL, 4.83 mmol) slowly at 0C. The reaction mixture stirred for 1 hour at 0C and then at room temperature for about 1 hour. The reaction mixture was quenched with saturated NH4CI solution (25 mL), extracted with ethyl acetate (3 x 150 mL), the organic layer was dried over Na2S04 and concentrated under reduced pressure to obtain crude product. The crude product was purified by flash chromatography (100-200 mu; 30% ethyl acetate in hexane) to afford l-(2-(4-fluorophenyl)thiazol-5-yl)ethanol as light yellow solid (420 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6): delta 7.93 (t, 2H), 7.67 (s, 1H), 7.30 (t, 2H), 5.71 (d, 1H), 5.01 (t, 1H), 1.45 (d, 3H); LC-MS m/z calculated for [M+H]+ 224.05, found 224.4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 85℃; for 6h;Inert atmosphere; | To a solution of 2-bromothiazole-5-carbaldehyde (5.0 g, 26.04 mmol) in toluene (150 mL) and ethanol (75 mL) was added (4-fluorophenyl)boronic acid (7.29 g, 52.08 mmol), 2M sodium carbonate solution (73.58 mL), Pd(PPh3)4 (1.5 g, 1.3 mmol) under argon atmosphere. The resulting mixture was heated at 85C for 6 h. The reaction mixture was concentrated under reduced pressure, the residue was diluted with water (150 mL), and extracted with ethyl acetate (5 x 500 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced pressures to obtain crude product. The crude product was purified by Combiflash chromatography (Mobile phase: 10% ethyl acetate in hexane) to give 2-(4- fluorophenyl)thiazole-5-carbaldehyde as off-white solid (200 mg, 88% yield). IH NMR (400 MHz, DMSO-d6): delta 10.06 (s, IH), 8.74 (s, IH), 8.14-8.11 (m, 2H), 7.39 (t, 2H); LC-MS m/z calculated for [M+H]+ 208.02, found 207.9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | To a mixture of 31c (1.56 g, 8.76 mmol) in THF (60 mL) was added a 2.5 M solution of n-BuLi (3.86 mL, 9.64 mmol) at -78C under N2. The mixture was agitated for 2 hours at this temperature then DMF (0.83 g, 11.4 mmol) was added. The mixture was stirred at 25C for 1 hour. Quenched with NH4C1 saturate solution and extracted with EtOAc. The organic layer was dried over sodium sulfate, and concentrated in vacuo and purified using Si02 chromatography to provide compound 31d (1.8 g, 100% yield). 1H NMR (CDC13) 5: 10.03 (s, 1 H), 8.40 (s, 1 H), 8.03-8.00 (m, 2 H), 7.24-7.15 (m, 2 H) | |
100% | To a mixture of 31c (1.56 g, 8.76 mmol) in THF (60 mL) was added a 2.5 M solution of n-BuLi (3.86 mL, 9.64 mmol) at -78C under N2. The mixture was agitated for 2 hours at this temperature then DMF (0.83 g, 11.4 mmol) was added. The mixture was stirred at 25C for 1 hour. Quenched with H4C1 saturate solution and extracted with EtOAc. The organic layer was dried over sodium sulfate, and concentrated in vacuo and purified using Si02 chromatography to provide compound 31d (1.8 g, 100% yield). 1H MR (CDC13) 5: 10.03 (s, 1 H), 8.40 (s, 1 H), 8.03-8.00 (m, 2 H), 7.24-7.15 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With trifluoroacetic acid; In acetonitrile; at 25℃; for 1h; | To a mixture of 3 Id (2.2 g, 10.7 mmol) and Core2 (3.66 g, 10.7 mmol) in anhydrous CH3CN (60 mL) was added TFA (0.37 g, 3.2 mmol). The mixture was stirred at 25C for 1 hour. The reaction mixture became a clear solution and then solid appeared. The solid was collected by filtration and washed with CH3CN to provide31e (4.35 g, 76% yield). 1H NMR (CDC13) delta: 7.83-7.79 (m, 2 H), 7.69 (s, 1 H), 7.24 (d, / = 8 Hz, 1 H), 7.20 (s, 1 H), 7.05 (t, / = 16 Hz, 2 H), 6.82 (s, 1 H), 6.77 (d, / = 8 Hz, 1 H), 6.65 (s, 1 H), 6.59 (d, / = 12 Hz, 1 H), 5.07 (d, / = 8 Hz, 1 H), 3.57-3.51 (m, 1 H), 3.23 (d, / = 16 Hz, 1 H) |
76% | With trifluoroacetic acid; In acetonitrile; at 25℃; for 1h; | To a mixture of 31d (2.2 g, 10.7 mmol) and Core2 (3.66 g, 10.7 mmol) in anhydrous CH3CN (60 mL) was added TFA (0.37 g, 3.2 mmol). The mixture was stirred at 25C for 1 hour. The reaction mixture became a clear solution and then solid appeared. The solid was collected by filtration and washed with CH3CN to provide31e (4.35 g, 76% yield). 1H MR (CDC13) delta: 7.83-7.79 (m, 2 H), 7.69 (s, 1 H), 7.24 (d, J= 8 Hz, 1 H), 7.20 (s, 1 H), 7.05 (t, J= 16 Hz, 2 H), 6.82 (s, 1 H), 6.77 (d, J = 8 Hz, 1 H), 6.65 (s, 1 H), 6.59 (d, J= 12 Hz, 1 H), 5.07 (d, J= 8 Hz, 1 H), 3.57-3.51 (m, 1 H), 3.23 (d, J= 16 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a slurry of zinc powder (10 eq) in THF (1M) was added TMSC1 (0.05 eq)and 1,2-dibromoethane (0.05 eq), and the slurry was briefly heated to reflux. To thissolution was added the appropriate halide (5 eq) at rt. After 30 mm, the solution wastreated with either Intermediate 6 or 4-bromo-2,6-diaminopyridine (1.0 eq), followed by tris(dibenzylidineacetone)dipalladium (0.05 eq) and (tri-tert-butylphosphonium) tetrafluoroborate (0.1 eq) in THF (0. 1M). The solution was allowed to stir 1-24 h, then concentrated and purified by column chromatography or preparative HPLC to furnish thealkylated pyridines; From <strong>[914348-80-4]2-(4-fluorophenyl)thiazole-5-carbaldehyde</strong>. Diazene reduction wascarried out using Zn/HOAc according to the alternate diazene reduction procedure B.MS(ESI) m/z 327.1 (M+H)t ?HNMR(500MF-Tz, DMSO-d6) oe 7.95 (dd, J=8.8, 5.5 Hz, 2H), 7.84 (s, 1H), 7.32 (t, J=8.8 Hz, 2H), 6.41 (br. s, 1H), 4.57 (br. s, 2H). Analytical HPLC: RT = 5.9 mm (Method A). |