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CAS No. : | 5122-94-1 |
Formula : | C12H11BO2 |
M.W : | 198.03 |
SMILES Code : | C2=C(C1=CC=CC=C1)C=CC(=C2)B(O)O |
MDL No. : | MFCD00093311 |
InChI Key : | XPEIJWZLPWNNOK-UHFFFAOYSA-N |
Pubchem ID : | 151253 |
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 |
---|---|---|
The mixture of 5-bromo-imidazo[1,2-a]pyrazine-2-carboxylic acid ethyl ester (0.3 g, 0.0011 mol), 3-biphenyl boronic acid (0.329 g, 0.0017 mol), (2',6'-dimethoxy-biphenyl-2-yl)- dicyclopentadienyl-phosphane (0.091 g, 0.00022 mol), palladium acetate (0.025g, 0.00011 mol) and potassium phosphate (0.71 g, 0.0033 mol) in terahydrofuran (7 mL) was stirred at ambient temperature under continuous nitrogen flow for 20 hours. A solution of lithium hydroxide monohydrate (0.2g, 0.0048 mol) in 5 mL of water was added and the stirring at ambient temperature was continued for another 4 hours. The solvents were removed and the residue was subjected to to preparative RP-HPLC (10% to 40% acetonitrile/0.05M aqueous ammonium acetate, buffered to pH 4.5, over 30 min at 21 mL/min; No. = 254 nm; Microsorb C18, 100 A, 5 mum, 250 x 46 mm column) to yield 5-biphenyl-4-ylmethyl-imidazo[1,2- a] pyrazine-2-carboxylic acid (0.049 g, 0.00016 mol) as an off-white solid. Retention time - 1.22 min., RP-HPLC (30% to 95% acetonitrile/0.01M aqueous ammonium acetate, buffered to pH 4.5, over 4.5 min at 0.8 mL/min; No. = 190-700 nm; Genesis C18,120 A, 4 mum, 33 x 4.6 mm column.). m/z: (M - H)-314. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;FibreCat; In ethanol; water; at 110℃; for 0.13333299999999998h;Microwave irradiation; | A 5 mL Biotage microwave vial was charged with FibreCat (Aldrich, 0.4 mmol/g; 37.5 mg, 3 mol%) and biphenyl-4- boronic acid (1 19.0 mg, 0.600 mmol). A solution of S-chloro^-iodo^-nitro-phenylamine (Intermediate 1, 149.0 mg, 0.500 mmol) in EtOH (4.4 mL) was added followed by IM aqueous K2CO3 (0.6 mL). The vial was heated in a microwave synthesizer (Biotage Initiator) at 1100C for 8 min. Contents of the vial were diluted with EtOAc (2 mL) and filtered. The resulting precipitate was washed with EtOAc (three times, 2 mL). The filtrate and washes were combined and evaporated to dryness in vacuo. The residue was dissolved in EtOAc (4 mL), washed with 1 M aqueous K2CO3 (twice, 1 mL) and evaporated to dryness in vacuo to give an orange-yellow solid. LR-MS (API-ES): calculated for Ci8Hi3ClN2O2 324.1, observed m/e 367.2 (100%), 347.0 ((M + Na)+, 325.0 (M + H)+, (Rt 3.56 min). The crude product was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 7h;Reflux; Inert atmosphere; | A mixture of <strong>[16499-62-0]4-chloro-7-fluoroquinazoline</strong> (0.516 g, 2.83 mmol), 4-biphenylboronic acid (0.621 g, 3.13mmol), potassium carbonate (1.018 g, 7.37 mol) and 3 mol% of tetrakis(triphenylphosphine)palladium(0)(0.114 g, 0.0986 mmol) in toluene (15 mL) was refluxed for 7 h, and poured into ice water. Then, thereaction mixture was extracted with EtOAc, washed with brine, and dried over Na2SO4. The residue wasfiltered, evaporated, and purified by silica gel column chromatography (n-hexane: EtOAc = 3:1) to affordcompound 28 as a white solid (0.714 g, 84%); mp 152-153 C; 1HNMR (500 MHz, CDCl3) δ 9.37 (s,1H), 8.26 (dd, J = 9.2, 6.3 Hz, 1H), 7.81-7.87 (m, 4H), 7.75 (dd, J = 9.5, 2.6 Hz, 1H), 7.68-7.70 (m, 2H),7.51 (t, J = 7.7 Hz, 2H), 7.41-7.44 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 167.8, 165.4 (d, J = 256.7 Hz),155.6, 152.9 (d, J = 14.4 Hz), 143.2, 140.1, 135.7, 130.4, 130.0 (d, J = 10.8 Hz), 129.0, 128.0, 127.4,127.2, 120.4, 118.3 (d, J = 25.2 Hz), 112.7 (d, J = 19.2 Hz); HRMS (FAB): m/z [M + H] + calcd forC20H14FN3: 301.1141; found: 301.1118. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; at 80℃; for 4h; | General procedure: To a solution of <strong>[474706-74-6]6-bromo-3-iodoimidazo[1,2-a]pyridine</strong> (33 mg, 0.1 mmol) were added arylboronic acid (0.11 mmol), K2CO3 (55 mg, 0.4 mmol), and PdCl2(dppf)?CH2Cl2 (4mg, 0.005 mmol). The resulting mixture was stirred at 80 c for 4 h and then cooled to rt. After removal of the solvent, the residue was purified by flash column chromatography (1420) (MeOH:CH2Cl2, 1:50) to give products. (1421) 1H NMR (CDCl3, 400 MHz) delta 7.56-7.68 (m, 5H), 7.72-7.80 (m, 3H), 7.56-7.68 (m, 5H), 7.46-7.52 (m, 2H), 7.36-7.42 (m, 1H), 7.24-7.30 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
109 mg | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide; In tert-Amyl alcohol; at 50℃; for 20h;Inert atmosphere; | General procedure: Amixture of phenylboronic acid (1a) (1 mmol, 122 mg), alpha-trifluoromethylacrylicacid (2) (0.5 mmol, 70 mg), [Cp*RhCl2]2 (0.01 mmol, 6 mg), AgSbF6 (0.1 mmol, 34mg), Ag2O (1 mmol, 232 mg), and 1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in tert-amylalcohol (3 ml) under argon at 50 C for 20 h.Then the reaction mixture was diluted by ethyl acetate (30 ml). The organiclayer was washed by 1 N HCl(30 ml), water 30 (ml), and brine (30 ml) and driedover Na2SO4. After evaporation of the solvents under vacuum, product 3a? (101 mg,93%) was isolated by column chromatography on silica gel usinghexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent. |