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CAS No. : | 151169-75-4 | MDL No. : | MFCD01074646 |
Formula : | C6H5BCl2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JKIGHOARKAIPJI-UHFFFAOYSA-N |
M.W : | 190.82 | Pubchem ID : | 2734330 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | 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 |
---|---|---|
sodium carbonate; tetrakis(triphenylphosphine)palladium (0); In toluene; | Step (a) Preparation of 4-(3',4'-Dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester In a manner similar to Example 12, Step (b), (3,4-dichloro-phenyl)boronic acid (1.0569 g, 0.005539 mol) was allowed to react with 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (1.3636 g, 0.005019 mol) in the presence of tetrakis(triphenylphosphine)palladium(0) (0.1054 g, 0.0000912 mol) and 2.0 M aqueous sodium carbonate (5.5 mL, 0.011 mol) in toluene (11 mL) to give, after chromatography on silica gel (270 g, 230-400 mesh), eluding with hexanes-acetone (7:1) 1.432 g of 4-(3',4'-dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 120-121 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate; In 1,4-dioxane; water; at 100.0℃; for 16.0h;Inert atmosphere; | (1207) To the iodo compound 389 (30 mg, 0.16 mmol), in dioxanewater (31 ml), 3,4-dichloro phenyl boronic acid (37 mg, 0.19 mmol), sodium acetate (62 mg, 0.76 mmol) and PdCl2(dppf) (23 mg, 0.03 mmol) were added. Then the reaction mixture was heated to 100 C. for 16 h. Then reaction mixture was cooled and diluted with ethyl acetate. Organic layer was separated and washed with water, brine and dried. Crude residue was column chromatographed to yield 390 (3-(3,4-dichlorophenyl)-6-(trifluoromethyl)-1H-indazole) in 65% yield. 1H NMR (CDCl3): 10.41 (br s, 1H), 8.1 (m, 2H), 7.68-7.72 (m, 2H), 7.60 (m, 1H), 7.53 (d, 1H). Mass spectrum (ESI+): m/z=331 [M+1]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
520 mg | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 100℃; for 1h;Inert atmosphere; Microwave irradiation; | The compound of Reference Example 4 (600 mg), 3,4-dichlorophenylboronic acid (635 mg), tetrakis (triphenylphosphine) palladium (175 mg) and sodium carbonate(803 mg) in tetrahydrofuran / water mixed solution (10.1 mL / 5 mL)Were stirred at 100 C. for 1 hour under a nitrogen atmosphere using a microwave reactor. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane / ethyl acetate) to give the title compound (520 mg) as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; | General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography. |
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