Structure of 1028263-94-6
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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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CAS No. : | 1028263-94-6 |
Formula : | C7H6FIO |
M.W : | 252.02 |
SMILES Code : | COC1=CC=C(F)C(I)=C1 |
MDL No. : | MFCD16295276 |
InChI Key : | YVAOSHLRHPIXQT-UHFFFAOYSA-N |
Pubchem ID : | 10490990 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
13% | With potassium phosphate; copper(l) iodide; dimethylethanolamine; at 60℃; for 24h; | [002 12j 1 OA. (S)-( 1 -(2-Fluoro-5 -methoxyphenyl)pyrrolidin-3 -yl)methanol: A mixture of <strong>[1028263-94-6]1-fluoro-2-iodo-4-methoxybenzene</strong> (187 mg, 0.74 1 mmol), (S)-pyrrolidin-3-ylmethanol (150 mg, 1.48 mmol), Cul (14 mg, 0.074 mmol) and K3P04 monohydrate (342 mg, 1.48 mmol) in dimethylethanolamine (0.7 mL, 7 mmol) was heated to 60 C for 24 h. The reaction was quenched with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the organic layer was washed with brine, dried (MgSO4), and concentrated. Purification via silica chromatography gave 1OA (22 mg, 0.098 mmol,13% yield). LC-MS Anal. Calc’d for C12H16FN02: 225.25, found [M+H] 226.3. 1HNMR (400 MHz, CDC13) ö 6.88 (dd, J=13.4, 8.6 Hz, 1H), 6.31 - 6.08 (m, 2H), 3.80 -3.75 (s, 3H), 3.72 - 3.64 (m, 2H), 3.55 - 3.43 (m, 2H), 3.42 - 3.34 (m, 1H), 3.29 - 3.21 (m,1H), 2.57 - 2.44 (m, 1H), 2.15 - 2.06 (m, 1H), 1.77 (dd, J=12.5, 7.7 Hz, 1H), 1.64 (br. s,1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | With tripotassium phosphate tribasic; copper (I) iodide; In N,N-dimethyl-formamide; at 85℃;Inert atmosphere; | A mixture of Intermediate 10 (250 mg, 0.97 mmol), 4-fluoro-3-iodo-1- methoxybenzene (319 mg, 1.27 mmol), N1,N2-dimethylethane-1,2-diamine (32 mg, 0.36 mmol), CuI (21 mg, 0.11 mmol), K3PO4 (413 mg, 1.95 mmol), and DMF (3 mL) was degassed by bubbling N2 through the suspension for 10 min, heated at 85 for 2 days, allowed to cool to room temperature, diluted (20 mL EtOAc), washed (20 mL water and then 20 mL brine), dried (Na2SO4), and then concentrated. The residue was purified by silica gel chromatography (0-15% EtOAc/hexanes) to give 5-(3-chloro-4-methoxyphenyl)-1-(2-fluoro- 5-methoxyphenyl)-1H-indazole (70 mg, 19%) as a white solid. LCMS: 383.0 [M+H]+. |
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