2-(N,N-DIMETHYLAMINOMETHYL)PHENYLBORONIC ACID

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 525 mg (1.48 mmol) tert-butyl[1-(4-bromo-phenyl)-5-oxo-pyrrolidin-3-yl]-carbamate are dissolved in 30 ml of toluene and 5 ml of water and combined with 318 mg (1.77 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid, 48 mg (0.15 mmol) tetrabutylammonium bromide and 314 mg (2.96 mmol) potassium carbonate, and lastly 173 mg (0.15 mmol) tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is refluxed for 90 minutes at 400 Watt in the microwave. Then another 330 mg (1.84 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid are added and the mixture is heated for one hour at 400 Watt in the microwave. The reaction solution is evaporated to dryness i. vac. The residue is purified by reversed phase chromatography. are added The reaction solution is refluxed for 90 minutes at 400 Watt in the microwave the mixture is heated for one hour at 400 Watt in the microwave The reaction solution is evaporated to dryness i The residue is purified by reversed phase chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 525 mg (1.48 mmol) tert-butyl[1-(4-bromo-phenyl)-5-oxo-pyrrolidin-3-yl]-carbamate are dissolved in 30 ml of toluene and 5 ml of water and combined with 318 mg (1.77 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid, 48 mg (0.15 mmol) tetrabutylammonium bromide and 314 mg (2.96 mmol) potassium carbonate, and lastly 173 mg (0.15 mmol) tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is refluxed for 90 minutes at 400 Watt in the microwave. Then another 330 mg (1.84 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid are added and the mixture is heated for one hour at 400 Watt in the microwave. The reaction solution is evaporated to dryness i. vac. The residue is purified by reversed phase chromatography. are added The reaction solution is refluxed for 90 minutes at 400 Watt in the microwave the mixture is heated for one hour at 400 Watt in the microwave The reaction solution is evaporated to dryness i The residue is purified by reversed phase chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the procedure described in Example 1, Step 10, using 1-{4′-[4-(3-bromo-phenylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester and 2-(N,N-dimethylaminomethyl)-phenylboronic acid. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) was used in place of tetrakis(triphenylphosphine)palladium(0). Prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 mg of ethyl 8-chloro-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate was suspended in 1 ml of toluene. 0.5 ml of ethanol, 0.25 ml of 2 M aqueous sodium carbonate solution, 61 mg of 2-(N,N-dimethylaminomethyl)phenylboronic acid and 10 mg of bis(triphenylphosphine)palladium (II) chloride were added to the obtained solution, and they were heated under reflux in argon atmosphere for 38 hours. Ethyl acetate was added to the reaction mixture. The organic layer was taken, washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resultant residue was purified by the silica gel column chromatography (eluent: chloroform/acetone=4/1) to obtain 59 mg of 1-cyclopropyl-8-(2-dimethylaminomethylphenyl)-9-methoxy-4-oxo-4H-quinolizine-3-carboxylic acid. were heated under reflux in argon atmosphere for 38 hours washed with water dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure The resultant residue was purified by the silica gel column chromatography (eluent: chloroform/acetone=4/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the procedure described in Example 1, Step 10, using 1-{4′-[4-(3-bromo-benzoylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester and 2-(N,N-dimethylaminomethyl)-phenylboronic acid. Prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the procedure described in Example 42, Step 2, using 1-{4′-[4-(3-bromo-phenylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester and 2-(N,N-dimethylaminomethyl)-phenylboronic acid. Prepared