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CAS No. : | 494747-09-0 | MDL No. : | MFCD11110207 |
Formula : | C7H5BrN2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WMFQSNQAZSEQQE-UHFFFAOYSA-N |
M.W : | 213.03 | Pubchem ID : | 52987774 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 toluene-4-sulfonic acid; at 130.0℃; for 1.0h; | Example A1; 6-Bromo-2-methyl-oxazolo[4,5-b]pyridine; A solution of 20 g (106 mmol) 2-amino-6-bromo-3-hydroxy-pyridine and 0.05 g p-toluenesulfonic acid monohydrate in 22 ml triethyl orthoacetate is stirred at 13O0C for 1 h. After cooling to room temperature the reaction solution is diluted with ethyl acetate (150 ml) and extracted with water (3 x 150 ml). The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. Subsequent purification by crystallization from ethanol affords the title compound (19 g) as yellow-orange crystals. The mass spectrum shows the molecular peak MH+ at 213.2 and 215.2 Da. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at -50.0℃; for 1.0h; | Example A2; 6-Bromo-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine; A stirred solution of 1.46 g (10.6 mmol) 4-methoxy-pyridine-2-aldehyde and 6.0 g (28.3 mmol) 6- bromo-2-methyl-oxazolo[4,5-b]pyridine (starting compound A1 ) in 2.8 ml tert-butanol and 11 ml absolute tetrahydrofuran is cooled to -5O0C. A solution of 1.55 g K-tert-butylate in 10 ml absolute tetrahydrofuran is slowly added to the reaction solution under stirring. After further stirring for 1 h, the reaction mixture is warmed to room temperature. For workup, the mixture is poured into a saturated aqueous NaHCO3 solution and then extracted three times with ethyl acetate. The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. Subsequent purification by silica gel chromatography [petrol ether/ethyl acetate (1/1 parts by volume)] affords the title compound (1.0 g) as yellow crystals of m.p. 159.80C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 75.0℃; for 12.0h;Inert atmosphere; | General procedure: Example 74 6-(6-fluoro-1H-indol-3-yl)-2-methyloxazolo[4,5-b]pyridine A mixture of <strong>[494747-09-0]6-bromo-2-methyl-oxazolo[4,5-b]pyridine</strong> (700 mg; 3.29 mmol; prepared as described in WO2007045622), tert-butyl 6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (892 mg; 2.47 mmol), Pd(PPh3)4 (288 mg; 0.25 mmol) and Na2CO3 (913 mg; 8.61 mmol) in DME (10 mL) and water (1 mL) was stirred at 75 C. for 12 hours under nitrogen. The reaction mixture was concentrated, redissolved in EtOAc, filtered through a short plug of silica, concentrated, and purified by preparative HPLC to afford 12.6 mg (2%) of the title compound as a white solid. LC-MS: m/z 268.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta [ppm]: 11.60 (br s, 1H), 8.79 (d, J=2.0 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 7.90 (dd, J=8.8, 5.5 Hz, 1H), 7.87 (d, J=2.4 Hz, 1H), 7.27 (dd, J=9.9, 2.4 Hz, 1H), 6.98 (ddd, J=9.7, 8.8, 2.4 Hz, 1H), 2.69 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 120.0℃; for 16.0h;Inert atmosphere; | tert-butyl N-(2-methyloxazolo[4,5-b]pyridin-6-yl)carbamalze: a flame-dried Schlenk tube was loaded withPd2(dba)3 (77 mg, 0.084 mmol) and (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenyl-phosphane (122 mg, 0.21mmol) . The vial was purged with nitrogen and toluene (26 mL)was added. The solution was allowed to stir for 15 mm atrt. Following the order, tert-butyl carbamate (295 mg, 0.2.52mmol), C52C03 (1.36 g, 4.00 mmol) and <strong>[494747-09-0]6-bromo-2-methyl-oxazolo[4,5-b]pyridine</strong> (450 mg, 2.10 mmol) were added andthe mixture was degassed (vacuum/nitrogen 5-6 times) and putin the pre-heated bath. The resulting solution was stirred16 h at 120 C, filtered over a short pad of Celite usingAcOEt, and concentrated. The compound was obtained afterpurification by flash-column chromatography (alumina pH =7),eluting a gradient of 100% DCM to 10% of a solution of EtOH20% in DCM, as a yellow solid in 23% yield. ?H NNR (400 MHz,DMSO-d6) 6 9.79 (s, 1H), 8.40 (d, J = 2.3 Hz, 1H), 8.24 (5, |
23% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 120.0℃; for 16.0h; | A flame- dried Schlenk tube was loaded with Pd2(dba)3 (0.077 g, 0.084 mmol) and (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)- diphenyl-phosphane (0.122 g, 0.21 mmol). The vial was purged with nitrogen and toluene (26 mL) was added. The solution was allowed to stir for 15 min at room temperature. Following the order, tert-butyl carbamate (0.295 g, 2.52 mmol), Cs2CO3 (1.36 g, 4.00 mmol) and 6-bromo-2-methyl-oxazolo[4,5- b]pyridine (0.45 g, 2.10 mmol) were added and the mixture was degassed (vacuum/nitrogen 5-6 times) and put in the pre- heated bath. The resulting solution was stirred 16 h at 120C, filtered over a short pad of Celite using AcOEt, and concentrated. The compound was obtained after purification by flash-column chromatography on neutral alumina gel (pH =7), eluting with a gradient of 100% DCM to 10% of a solution of EtOH 20% in DCM, as a yellow solid in 23% yield. 1H NMR (400 MHz, DMSO-d6) delta 9.79 (s, 1H), 8.40 (d, J = 2.3 Hz, 1H), 8.24 (s, 1H), 2.63 (s, 3H), 1.49 (s, 9H). |
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