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In an argon atmosphere, 100 mL of dehydrated THF were added to 10 g (20 mmol) of 2-bromo-9,10-di(2-naphtyl) anthracene, and the temperature of the mixture was cooled to -78 C. Then, 14 mL of n-butyllithium (in hexane, 1.6 mol/L) were dropped. After the mixture had been stirred at -78 C for 1 hour, the temperature of the mixture was increased to 0C. The temperature of the mixture was cooled to -78 C again, and 6.6 mL (60 mmol) of trimethoxyborane were added. The mixture was stirred at -78 C for 1 hour, and was then stirred at room temperature for 2 hours. 100 mL of 10-mass% hydrochloric were added, and the whole was stirred for 1 hour, followed by filtration. The resultant solid was washed with toluene to obtain 4.7 g of 9,10-diphenylanthracene-2-boronic acid (50% yield).
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;
(9,10-di(naphthalen-2-yl)anthracen-2-yl)boronic acid 2-bromo-9,10-di(naphthalen-2-yl)anthracene (10.00 g, 1.0 eq, 19.63 mmol) was dissolved in THF (140 mL) and cooled to -78 C. At this temperature n-BuLi (2.5M in hexane, 10.2 mL, 1.3 eq, 25.52 mmol) was added dropwise and the mixture was stirred for 2 hours. Afterwards, B(OMe)3 (6.12 g, 3.0 eq, 58.89 mmol) was added at -78 C. and the reaction mixture was allowed to warm up to room temperature. After stirring for 17 hours the mixture was quenched with HCl, the yellow precipitate was filtered off and washed with water (2*30 mL). The residue was dried in vacuo and used without further purification. Yield: 9.8 g (yield 100%)
With hydrogenchloride; n-butyllithium;
(9,10-di(naphthalen-2-yl)anthracen-2-yl)boronic acid Prepared according to procedure described in EP13170862: 2-bromo-9,10-di(naphthalen-2-yl)anthracene (10.00 g, 1.0 eq, 19.63 mmol) was dissolved in THF (140 mL) and cooled to -78 C. At this temperature n-BuLi (2.5M in hexane, 10.2 mL, 1.3 eq, 25.52 mmol) was added dropwise and the mixture was stirred for 2 hours. Afterwards, B(OMe)3 (6.12 g, 3.0 eq, 58.89 mmol) was added at -78 C. and the reaction mixture was allowed to warm up to room temperature. After stiffing for 17 hours the mixture was quenched with HCl, the yellow precipitate was filtered off and washed with water (2*30 mL). The residue was dried in vacuo and used without further purification. Yield: 9.8 g (100%)
Prepared according to procedure described inEP13 2-bromo-9, 1 0-di(naphthalen-2-yl)anthracene (10.00 g, 1.0 eq, 19.63 mmol) was dissolved in THF (140 mE) and cooled to -78 C. At this temperature n-BuEi (2.5M in hexane, 10.2 mE, 1.3 eq, 25.52 mmol) was added dropwise and the mixture was stirred for 2 hours. Afterwards, B(OMe)3 (6.12 g, 3.0 eq, 58.89 mmol) was added at -78 C. and the reaction mixture was allowed to warm up to room temperature. After stirring for 17 hours the mixture was quenched with HC1, the yellow precipitate was filtered off and washed with water (2x30 mE). The residue was dried in vacuo and used without further purification. Yield: 9.8 g (100%)
70%
Synthesis of Intermediate 1c; 5 g of Intermediate 1b (9.81 mmol) was dissolved in 70 ml of THF dried under nitrogen atmosphere, and 4.7 ml of lithium butyl (11.8 mmol) was added to the mixture at -78 C. The mixture was stirred for one hour at the same temperature, and then 2.20 ml of trimethyl borate (29.4 mmol) was added to the mixture. The temperature of the mixture was increased to room temperature, and one hour later, 2N of an aqueous hydrochloric acid solution was added to the mixture and stirred for 3 hours. The obtained solid compound was filtered while being washed with toluene to obtain 3.27 g of light-yellow Intermediate 1c (yield 70%).
70%
Synthesis of Intermediate 1c; 5 g of Intermediate 1b (9.81 mmol) was dissolved in 70 ml of THF dried under nitrogen atmosphere, and 4.7 ml of lithium butyl (11.8 mmol) was added to the mixture at -78C. The mixture was stirred for one hour at the same temperature, and then 2.20ml of trimethyl borate (29.4 mmol) was added to the mixture. The temperature of the mixture was increased to room temperature, and one hour later, 2N of an aqueous hydrochloric acid solution was added to the mixture and stirred for 3 hours. The obtained solid compound was filtered while being washed with toluene to obtain 3.27 g of light-yellow Intermediate 1c (yield 70%).
70%
Synthesis of Intermediate 1c; The intermediate 1b (5g, 9.81 mmol) was dissolved in 70 ml of dried THF under a nitrogen atmosphere, and butyl lithium (4.7ml, 11.8mmol) was added dropwise thereto at -78 C. The reaction mixture was stirred at -78 C for one hour, and trimethylborate (2.20ml, 29.4mmol) was added thereto. The reaction solution was heated to room temperature and incubated for one hour. Then, a 2N HCl solution was added thereto, and the resultant solution was stirred for three hours. The resultant solid compound was washed and filtered with toluene to yield intermediate 1c as a light yellow powder (3.27g, yield: 70%).
Synthesis of Intermediate 1c; 5 g (9.81 mmol) of Intermediate 1b was dissolved in 70 ml of dried THF under a nitrogen atmosphere and 4.7 ml (11.8 mmol) of butyl lithium was added thereto at -78C. The resulting product was stirred at the same temperature for 1 hour, and 2.20ml (29.4 mmol) of trimethyl borate was added thereto. The temperature of the mixture was raised to room temperature, a 2N HCl solution was added thereto after 1 hour, and the mixture was stirred for 3 hours. The resulting solid compound was filtered while washing with toluene to obtain 3.27 g of yellow Intermediate 1c (Yield: 70%).
3-2) Synthesis of 2-bromo-9,10-di(2-naphthyl)anthracene 190 g (0.37 mol) of 2-bromo-9,10-di(2-naphthyl)anthracene obtained from 3-1) was dissolved with 1.5 L of THF in a 5L flask and the temperature was cooled to -78C. Then, 279 ml (0.44 mol) of 1.6 M n-BuLi was slowly added dropwise thereto. After one hour, 140 g (0.74 mol) of B(OiPr)3 was slowly added dropwise thereto and the temperature was raised to room temperature and the mixture was stirred. 1 L of 2N HCl(aq) was added to the resultant mixture at a temperature of 0C and then the mixture was extracted using EA. An organic layer was dried over MgSO4 and then re-crystallized with EA/hexane, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (150 g, 84%).
5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-7,7-di-methyl-5,7-dihydroindeno[2,1-b]carbazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium tert-butylate; palladium diacetate; In 1,3,5-trimethyl-benzene; for 8h;Reflux; Inert atmosphere;
In a three-necked flask,2-bromo-9,10-di(2-naphthyl)anthracene (0.53 g, 1.05 mmol) was added,Intermediate 2-2 (0.30 g, 1.05 mmol), potassium tert-butoxide (0.22 g, 2 mmol), palladium acetate (10 mg), S-phos (36 mg) and 30 ml1,3,5-Trimethylbenzene is heated under reflux with nitrogen for 8 hours, cooled, washed with water and dried. The crude product is purified by column chromatography to give 0.4 g of product.Product, yield, 53%
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