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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 15164-44-0 |
Formula : | C7H5IO |
M.W : | 232.02 |
SMILES Code : | C1=C(C=CC(=C1)I)C=O |
MDL No. : | MFCD00039576 |
InChI Key : | NIEBHDXUIJSHSL-UHFFFAOYSA-N |
Pubchem ID : | 96657 |
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 |
---|---|---|
25% | With copper(I) oxide; In N,N-dimethyl acetamide; at 190℃; for 72h; | A DMAc solution (60 mL) of 4-iodobenzaldehyde (3.48 g,15.00 mmol), carbazole (3.01 g, 18.00 mmol), and copper(I) oxide (2.57 g, 18.00 mmol) was stirred at 190 Cfor 3 days. After cooling to room temperature, the productmixture was washed with water. After removal ofthe organic solvent, the residue was purified by columnchromatography on silica gel using methylene chlorideand n-hexane (1:5, v/v) as an eluent. Further purificationwas performed by precipitation in n-hexane to obtain1 as a light yellow solid. Yield (1.02 g, 25%). mp160-162 C. 1H NMR (400 MHz, DMSO-d6) 7.33(t, 2 H, -Ph-carbazole), 7.46 (t, 3 H, -Ph-carbazole),7.52 (d, 2 H, -Ph-carbazole), 7.91 (d, 2 H, -carbazole-Ph), 8.20 (d, 2 H, -carbazole-Ph), 8.27 (d, 2 H, -Ph-carbazole), 10.12 (s, 1 H, -Ph-CHO); 13C NMR(100.64 MHz, DMSO-d6) 100.86, 120.67, 120.78,123.24, 126.53, 126.72, 131.41, 134.58, 139.45, 142.20,192.23. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 35Preparation of Compound 110: (E)-Ethyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate hydrochlorideStep 1: (E)-4-(2-(2-Chloro-4-fluorophenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1,1-indazol-5-yl)but-1-en-1-yl)benzaldehyde A round-bottom flask equipped with a magnetic stir bar, a reflux condenser, internal thermometer, and a N2 inlet was charged with 5-(but-1-yn-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (50.0 g, 197 mmol; Intermediate 3), bis(pinacolato)diboron (50.4 g, 199 mmol), and anhydrous 2-methyltetrahydrofuran (393 mL) followed by Pt(PPh3)4 (1.83 g, 1.5 mmol). This mixture was degassed with three vacuum/N2 cycles, heated at 83 C. (internal temperature; oil bath at 95 C.) for 5 h under N2, and then allowed to cool to room temperature. 2-Methyltetrahydrofuran (393 mL), cesium carbonate (128.1 g, 393 mmol), and water (11.8 mL, 1.5% v/v) were added, and the reaction was cooled to 4 C. 4-Iodobenzaldehyde (45.6 g, 197 mmol) and PdCl2(PPh3)2 (6.90 g, 9.8 mmol) were added, and the reaction was degassed with three vacuum/N2 cycles. The mixture was allowed to warm to room temperature and stirred overnight. Aqueous KOH solution (4M, 275 mL, 1100 mmol) and <strong>[101335-11-9]2-chloro-4-fluoroiodobenzene</strong> (70.6 g, 275 mmol) were added. The reaction was degassed with 3 vacuum/N2 cycles, heated at 75 C. (internal temperature; oil bath at 90 C.) for 7 h under N2, and then allowed to cool to room temperature. The layers were separated, and the organic layer was washed with brine (800 mL), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel chromatography (0-20% ethyl acetate in hexanes) to give the title compound (82.6 g, 7:1 mixture of regioisomers) as a pale yellow foam. Data for major isomer; (E)-4-(2-(2-chloro-4-fluorophenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)benzaldehyde: 1H NMR (300 MHz, DMSO-d6): delta 9.82 (s, 1H), 8.15 (s, 1H), 7.78-7.71 (m, 2H), 7.61 (d, 2H), 7.43-7.27 (m, 3H), 7.15 (m, 3H), 5.86 (dd, 1H), 3.93-3.85 (m, 1H), 3.79-3.68 (m, 1H), 2.44-2.36 (m, 3H), 2.10-1.96 (m, 2H), 1.81-1.67 (m, 1H), 1.63-1.53 (m, 2H), 0.92 (t, 3H); LCMS: 405 [(M-THP+H)+H]+. |