(2,5-difluorophenyl)boronic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of [3-[2-[4-(5-bromothiazole-2-yl)-2,6-dimethyl piperazine-1-yl]ethoxy]-4-methylphenyl]acetic acid (400 mg), 2,5-difluorophenyl boronic acid (270 mg), tetrakis(triphenylphosphine) palladium (100 mg), 1M sodium carbonate (4.3 mL) and dimethylformamide (8 mL) was reacted with a microwave reaction device at 180° C. for 5 minutes. To the reaction solution was added water and extracted with chloroform. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel to give the title compound (369 mg). Yield: 87%. was reacted with a microwave reaction device at 180° C. for 5 minutes extracted with chloroform The organic layer was washed with water and brine dried over magnesium sulphate The solvent was evaporated under reduced pressure The residue was purified by column chromatograph on silica gel

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

Procedure: 5-(2,4-Difluorophenyl)-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone was prepared from 5-bromo-3,4-dihydro-7-methoxy-1-(3-methoxycarbonyl-6-methylphenyl)-2(1H)-quinolinone (INTERMEDIATE 14) and 2,5-difluorophenylboronic acid by a procedure analogous to that described in INTERMEDIATE 2. Mass spectrum (ESI) 438.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.06 (d, J=5.0 Hz, 1H); 7.89 (s, 1H); 7.42 (d, J=5.0 Hz, 2H); 7.01 (m, 2H); 6.49 (s, 1H); 5.86 (s, 1H); 3.95 (s, 3H); 3.68 (s, 3H); 2.81 (m, 4H); 2.21 (s, 3H).