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CAS No. : | 143468-13-7 | MDL No. : | MFCD06659667 |
Formula : | C7H5BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LKXJGVGBEDEAAW-UHFFFAOYSA-N |
M.W : | 197.03 | Pubchem ID : | 11159915 |
Synonyms : |
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Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P273-P280-P305+P351+P338 | UN#: | 3077 |
Hazard Statements: | H302-H317-H318-H411 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 zinc;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 140℃; for 4h;Inert atmosphere; | Acid-4: 3-Chloro-1 H-pyrrolo[2,3-b]pyridine-6-carboxylic acid; a) 1 H-Pyrrolo[2,3-b]pyridine-6-carbonitrile; To a mixture of 6-bromo-1 H-pyrrolo[2,3-b]pyridine (Synthesis, 1992, 661 , example 3b) (788 mg, 4 mmol), zinccyanide (329 mg, 2.80 mmol) and zinc dust (26.2 mg, 0.4 mmol) in dry DMF (12 ml) was added (dppf)PdCI2xCH2Cl2 adduct catalyst (163 mg, 0.2 mmol) under nitrogen. The mixture was heated at 140 C for 4 h. The reaction mixture was diluted with ethyl acetate and washed with aq. Saturated bicarbonate solution and brine, dried over sodium sulfate, filtered and evaporated. 1.04 g dark yellow oil. The crude product was chromatographed over silica gel (cyclohexane/ethyl acetate 3:1) to provide the title compound as a white solid.TLC Rf=0.35 (2: 1 cyclohexane:ethyl acetate);LC-MS: 0.81 min. (100% purity, ESI+ 144), API-ES+ 144;1H-NMR (400 MHz, CDCI3): delta 11.05 (s, 1 H, NH), 8.08 (d, 1 H), 7.71 (dd, 1 H), 7.52 (d, 1 H), 6.66 (m, 1 H). | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; zinc; In N,N-dimethyl-formamide; at 140℃; for 5h;Inert atmosphere; | A mixture of 6-bromo-1H-pyrrolo[2,3-b]pyridine (4.00 g, 20.30 mmol, 1.00 eq), Zn (132.75 mg, 2.03 mmol, 0.10 eq), Zn(CN)2(1.67 g, 14.21 mmol, 902.05 uL, 0.70 eq) and Pd(dppf)Cl2.CH2Cl2 (828.95 mg, 1.02 mmol, 0.05 eq) in DMF (10.00 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 140C for 5 h under N2 atmosphere. The reaction mixture was diluted with EtOAc (50 mL) and washed with aq. saturated bicarbonate solution (100 mL) and brine (100 mL*2), dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (SiO2, PE/EtOAc=10:1 to 3:1) to afford the title compound (1.50 g, 8.91 mmol, 43.88% yield, 85% purity) as a white solid. | |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; zinc; In N,N-dimethyl-formamide; at 140℃; for 5h;Inert atmosphere; | A mixture of 6-bromo-lH-pyrrolo[2,3-b]pyridine (10 g, 50.75 mmol, 1 eq), Zn (331.88 mg, 5.08 mmol, 0.1 eq), Zn(CN)2 (4.17 g, 35.53 mmol, 2.26 mL, 0.7 eq) and Pd(dppf)Cl2.CH2Cl2 (2.07 g, 2.54 mmol, 0.05 eq) in DMF (100 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at l40C for 5 h under N2 atmosphere. It was diluted with water (500mL) and EtOAc (300mL), and then filtered to remove the solid, the solid was washed with EtOAc (200mLx2). The combined organic layers were washed with brine (500 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, PE/EtOAc = 5/1 to 2/1) to afford the title compound (5.3 g, 89% purity) as a green solid |
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