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CAS No. : | 947533-45-1 | MDL No. : | MFCD09835164 |
Formula : | C4H2BrFN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ANSMRNCOBLTNBO-UHFFFAOYSA-N |
M.W : | 176.97 | Pubchem ID : | 26344048 |
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 |
---|---|---|
0.760 g | With (1,2-dimethoxyethane)dichloronickel(II); tris-(trimethylsilyl)silane; [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium hydroxide; In 1,2-dimethoxyethane; for 0.25h;Inert atmosphere; Irradiation; | A solution of NiCl2(glyme) (0.084 g, 0.384 mmol), 4-ie/7-butyl-2-(4-ie/7-butyl-2-pyridyl)pyridine, and Ir{dF(CF3)ppy}2(dtbpy)PF6(0.086 g, 0.077 mmol) in DME (80 mL) was sparged with N2for 15 min. The nickel solution was added to a mixture of //77-butyl 3- (bromomethyl)pyrrolidine-l-carboxylate (2.03 g, 7.68 mmol), 2-bromo-5-fluoro-pyrimidine (1.70 g, 9.61 mmol), tris(trimethylsilyl) silane (2.87 g, 11.5 mmol, 3.54 mL), and lithium hydroxide (0.736 mg, 30.7 mmol). After the mixture was sparged with N2(15 min), the reaction was irradiated with blue LEDs (48 watts 450 hv) overnight at 40 C. Celite was added to the reaction, and the mixture was filtered and concentrated in vacuo. The residue was purified over Si02(0-100% EtOAc:heptane) to afford the title compound (0.760 g). LCMS (ESI): [M - i-Bu] 226. 1HNMR: (500 MHz, CDCl3) d 8.39 (br d, 7=9.46 Hz, 2 H), 3.30 - 3.46 (m, 2 H), 3.10 - 3.21 (m, 1 H), 2.85 - 2.96 (m, 3 H), 2.54 - 2.66 (m, 1 H), 1.80 - 1.91 (m, 1 H), 1.42 - 1.57 (m, 1 H), 1.27 - 1.35 (m, 9 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 100℃; for 72.0h;Inert atmosphere; | To a mixture of <strong>[1015609-11-6]methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate</strong> (1.00 g, 5.68 mmol), 2-bromo-5-fluoropyrimidine (1.20 g, 6.81 mmol), K3PO4 (1.20 g, 5.68 mmol), (R,R)-N,N'-dimethylcyclohexane-1,2-diamine (0.323 g, 2.27 mmol) in toluene (57 mL) under N2 was added CuI (0.216 g, 1.13 mmol). The mixture was heated at 100 C. for 72 h. After cooling to RT, Celite was added, and the mixture was filtered and concentrated. The crude residue was purified by flash silica gel chromatography (0-100% EtOAc/hexanes) to afford the title compound. LC/MS=273 [M+1]. |
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