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With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In toluene; for 3h;Inert atmosphere; Reflux;
The compound <strong>[13438-50-1]3-bromofluoranthene</strong> (30 g, 98 mmol) and 2-amino-9,9-dimethylfluorene (20.5 g, 98 mmol) were completely dissolved in 200 ml of toluene in a nitrogen atmosphere and then NaOt-Bu (11.3 g, 117.6 mmol) The mixture was stirred while increasing the temperature. After refluxing began, Bis (tri-tert-butylphosphine) palladium (0) (0.5 g, 0.98 mmol) was slowly added dropwise. After 3 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure, and then subjected to column purification to obtain 31.9 g of intermediate A
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 100℃; for 20h;
5 grams (g) of <strong>[50548-45-3]1-bromodibenzo[b,d]furan</strong> (Intermediate (a)), 6.4 g of 9,9-dimethyl-9H-fluoren-2-amine (Intermediate (b)), 6.4 g of potassium tert-butoxide (KtOBu), 0.3 g of P(tBu)3, and 0.4 g of Pd2 (dba)3 were diluted in toluene, followed by stirring at a temperature of 100 C. under reflux. After a 20-hour lapse, the temperature was lowered to room temperature. Subsequently, the reaction was terminated utilizing water. An organic layer was extracted therefrom three times utilizing ethyl acetate. Then, the organic layer was dried utilizing anhydrous magnesium sulfate, followed by filtration under reduced pressure. The obtained residue was separated and purified through column chromatography to thereby obtain 6.5 g of Intermediate 1-1 (yield: 86%). The compound thus obtained was identified by liquid chromatography-mass spectrometry (LC-MS). C27H21NO: calc'd: M+375.16 foun'd: 375.26
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 105 - 110℃; for 2h;Inert atmosphere;
<strong>[26608-06-0]3-bromodibenzofuran</strong> (10.0 g, 40.5 mmol),2-bromo-9,9-dimethylhydrazine (9.3 g, 44.5 mmol),Tris(dibenzylideneacetone)dipalladium (0.4 g, 0.4 mmol),2-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (0.4 g, 0.8 mmol) and sodium tert-butoxide (5.8 g, 60.7 mmol) were added to toluene (100 mL).Heated to 105-110 C under nitrogen protection,After stirring for 2 hours; cooling to room temperature, the reaction solution was washed twice with water, dried over magnesium sulfate, filtered, and then filtered, and the filtrate was passed through a silica gel column, and the solvent was removed under reduced pressure. The crude product was recrystallized and purified using dichloromethane/n-heptane system. The pale yellow solid intermediate VII-B (12.1 g, 80%) was obtained.
2-bromo-7-adamantyl-9,9-dimethylfluorene[ No CAS ]
C52H47NO[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
Under nitrogen protection, 2-bromo-7-adamantyl-9,9-dimethylfluorene 82.797mmol, 2-amino-9,9-dimethylfluorene 82.797mmol, toluene 675mL,248.391mmol of sodium tert-butoxide, stir, heat up to 70 C, slowly add Pd2dba3 0.82797mmol, s-PHOS 1.6560mmol, after the addition, continue to warm to 105 C and reflux for 4h, then lower the temperature to 70 C, add 4- Brominated biphenyl 81.141 mmol, continued to warm to 105 C. and refluxed for 6 h. After the reaction was completed, the temperature was reduced, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%. Compound 9 was dried. Yield: 53%.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 95℃; for 24h;
9,9-dimethyl-9H-fluoren-2-amine (6.5g, 0.031mol / sigma aldrich), Pd (pph3) 4 (1.8g, 0.0015mol), in Intermediate 1-3 (10.0g, 0.031mol),TOL 300ml was added to potassium carbonate (12.8g, 0.0935mol) and reacted at 95 C for 24 hours. After the completion of the reaction, the mixture was cooled and separated by H20: MC, followed by column purification (n-Hexane: MC), to obtain 11.0 g (yield 79%) of intermediate 7-1.
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