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With water; potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100.0℃; for 4.0h;
A mixture of N-[5-(8-chloro-l,5-naphthyridin-2-yl)-3- pyridinyl] benzenesulf onamide (0.302 mmol), 4-((N,N- dimethylamino)methyl)phenylboronic acid hydrochloride (0.333 mmol), and dichloro[l,r-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.015 mmol) in saturated aqueous potassium carbonate solution (1 mL) and 1,4-dioxane (3 mL) was stirred at 100 0C for 4 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and water (10 mL), and then neutralized with 3 drops 6N aqueous HCl solution. The aqueous layer was back- extracted with ethyl acetate (10 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Purification by reverse phase HPLC (10-70% acetonitrile/water with 0.1% NH4OH) provided the title compound as a yellow solid (46%). MS(ES)+ m/e 496 [M+H]+
6-bromo-3-iodo-2-(naphthalen-1-ylmethoxy)quinoline[ No CAS ]
6-bromo-3-(4-((dimethylamino)methyl)phenyl)-2-(naphthalen-1-ylmethoxy)quinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
87.35%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 80.0℃; for 10.0h;
2- (1-Naphthylmethoxy)-6-bromo-3-iodoquinoline (100 mg, 0.21 mmol) was dissolved in 3 mL of toluene, Pd(PPh3)4 (13 mg, 0.01 mmol) was added successively, Sodium carbonate (65 mg, 0.62 mmol) in 1 mL of water,4-(dimethylaminomethyl)boronic acidHydrochloride (53 mg, 0.25 mmol),80 C stirring reaction for 10 hours,5 mL of water was added thereto, and the mixture was extracted three times with dichloromethane,The combined organic layers were subjected to column chromatography (dichloromethane / methanol 20: 1) to give 91 mg of a yellow oil, 87.35% yield.
6-methoxy-2-(1-naphthylmethoxy)-3-iodoquinoline[ No CAS ]
3-(4-N,N-dimethylaminomethyl)phenyl-6-methoxy-2-chloroquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
64.31%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 85.0℃; for 15.0h;
2-(1-Naphthylmethoxy)-6-methoxy-3-quinoline(150 mg, 0.34 mmol) was dissolved in 3 mL of toluene, Pd(PPh3)4 (20 mg, 0.02 mmol) was added sequentially,Sodium carbonate (130 mg, 1.23 mmol) in 2 mL of water,4-(dimethylaminomethyl)borate hydrochloride (88mg, 0.4lmmo 1) at 85 C for 15 hours, Add 5mL of water, dichloromethane extract three times, combine the organic phase, column chromatography (dichloromethane / methanol 20: 1)A white solid 98mg, yield 64.31%
3-(4-N,N-dimethylaminomethyl)phenyl-2-chloro-6-bromoquinoline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; at 90.0℃; for 20.0h;
2-Chloro-6-bromo-3-iodoquinoline (2.00 g, 5.45 mmol) was dissolved in 15 mL of toluene,Pd (PPh3) 4 was added sequentially(0.32 g, 0.27 mmol), sodium carbonate(1.73 g, 16.35 mmol) in 5 mL of water,4-dimethylaminomethylbenzeneboronic acid hydrochloride (1.4 g, 6.53 mmol),90 C stirring reaction for 20 hours,Add 20mL of water, dichloromethane extract three times, combine the organic phase, column chromatography (dichloromethane / methanol 15: 1),A white solid of 1.81 g, yield 88.80%
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