(2-methylsulfinylphenyl)boronic acid

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-[2-(3-Amino-6-bromo-pyrazin-2-yl)ethynyl]phenol (72 mg, 0.2482 mmol), (2-methylsulfinylphenyl)boronic acid (54.80 mg, 0.2978 mmol) and K3PO4 (105.4 mg, 0.4964 mmol) were combined in MeCN (2 mL)/water and Pd[P(tBu)3]2 (6.342 mg, 0.01241 mmol) was added. The reaction was heated at 60° C. for 15 hours. The reaction was cooled to ambient temperature and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) and freeze-dried to give the title product as a yellow solid (24 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.34 (s, 3H), 5.15 (d, 1H), 6.88 (dd, 1H), 7.09 (br s, 2H), 7.19 (d, 1H), 7.27 (t, 1H), 7.60-7.69 (m, 2H), 7.89 (d, 1H), 8.17 (d, 1H), 8.60 (s, 1H) and 9.76 (s, 1H) ppm; MS (ES+) 350.1. was added The reaction was cooled to ambient temperature The layers were separated the aqueous layer extracted with EtOAc (×3) The combined organic layers were dried (MgSO4) filtered concentrated in vacuo The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) freeze-dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-[2-(3-Amino-6-bromo-pyrazin-2-yl)ethynyl]phenol (72 mg, 0.2482 mmol), (2-methylsulfinylphenyl)boronic acid (54.80 mg, 0.2978 mmol) and K3PO4 (105.4 mg, 0.4964 mmol) were combined in MeCN (2 mL)/water and Pd[P(tBu)3]2 (6.342 mg, 0.01241 mmol) was added. The reaction was heated at 60° C. for 15 hours. The reaction was cooled to ambient temperature and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) and freeze-dried to give the title product as a yellow solid (24 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.34 (s, 3H), 5.15 (d, 1H), 6.88 (dd, 1H), 7.09 (br s, 2H), 7.19 (d, 1H), 7.27 (t, 1H), 7.60-7.69 (m, 2H), 7.89 (d, 1H), 8.17 (d, 1H), 8.60 (s, 1H) and 9.76 (s, 1H) ppm; MS (ES+) 350.1. was added The reaction was cooled to ambient temperature The layers were separated the aqueous layer extracted with EtOAc (×3) The combined organic layers were dried (MgSO4) filtered concentrated in vacuo The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) freeze-dried

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

Procedure: Essentially prepared according to Procedure F using 2,4-dichloro-5,7-difluoro-3-methylquinoline (250 mg, 1.00 mmol) and 2-(methylsulfinyl)phenylboronic acid to give 4-chloro-5,7-difluoro-3-methyl-2-(2-(methylsulfinyl)phenyl)quinoline. Mass Spectrum (ESI) m/e=352.1 (M+1). Essentially prepared

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-[2-(3-Amino-6-bromo-pyrazin-2-yl)ethynyl]phenol (72 mg, 0.2482 mmol), (2-methylsulfinylphenyl)boronic acid (54.80 mg, 0.2978 mmol) and K3PO4 (105.4 mg, 0.4964 mmol) were combined in MeCN (2 mL)/water and Pd[P(tBu)3]2 (6.342 mg, 0.01241 mmol) was added. The reaction was heated at 60° C. for 15 hours. The reaction was cooled to ambient temperature and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) and freeze-dried to give the title product as a yellow solid (24 mg, 26% Yield). 1H NMR (400.0 MHz, DMSO) δ 3.34 (s, 3H), 5.15 (d, 1H), 6.88 (dd, 1H), 7.09 (br s, 2H), 7.19 (d, 1H), 7.27 (t, 1H), 7.60-7.69 (m, 2H), 7.89 (d, 1H), 8.17 (d, 1H), 8.60 (s, 1H) and 9.76 (s, 1H) ppm; MS (ES+) 350.1. was added The reaction was cooled to ambient temperature The layers were separated the aqueous layer extracted with EtOAc (×3) The combined organic layers were dried (MgSO4) filtered concentrated in vacuo The residue was purified by column chromatography (ISCO Companion™, 12 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, dry loaded) freeze-dried