2-(2-FLUORO-4-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Conditions: temp:80.01; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:

Conditions: temp:50.01; 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: 2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (600 mg, 2.38 mmol), methyl 4-bromo-3-fluorobenzoate (665 mg, 2.856 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (292 mg, 0.358 mmol), potassium carbonate (2.38 ml, aq., 2M, 4.76 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 145° C. for 15 min. Aliquot indicated formation of the desired cpd. TLC (20% EtOAc/hex) indicated a bright purple spot @ Rf=0.4. Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=278.08; found=279.09 (M+1)+. irradiation at 145° C. for 15 min Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge) The column was eluted by a 0% to 20% EtOAc/hexanes mixture concentrated in vacuo

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

Procedure: 2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (600 mg, 2.38 mmol), methyl 4-bromo-3-fluorobenzoate (665 mg, 2.856 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (292 mg, 0.358 mmol), potassium carbonate (2.38 ml, aq., 2M, 4.76 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 145° C. for 15 min. Aliquot indicated formation of the desired cpd. TLC (20% EtOAc/hex) indicated a bright purple spot @ Rf=0.4. Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=278.08; found=279.09 (M+1)+. irradiation at 145° C. for 15 min Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge) The column was eluted by a 0% to 20% EtOAc/hexanes mixture concentrated in vacuo

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

Procedure: 2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (600 mg, 2.38 mmol), methyl 4-bromo-3-fluorobenzoate (665 mg, 2.856 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (292 mg, 0.358 mmol), potassium carbonate (2.38 ml, aq., 2M, 4.76 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 145° C. for 15 min. Aliquot indicated formation of the desired cpd. TLC (20% EtOAc/hex) indicated a bright purple spot @ Rf=0.4. Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=278.08; found=279.09 (M+1)+. irradiation at 145° C. for 15 min Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge) The column was eluted by a 0% to 20% EtOAc/hexanes mixture concentrated in vacuo

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

Procedure: 2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane were coupled in the same way as in Example 30 to give 2-[3-(2,2′-difluoro-4′-methoxybiphenyl-5-yl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]propan-2-ol as an off-white solid (5 mg, 3%): m/z (ES+) 413 [MH+].

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

Procedure: 2-(2-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (600 mg, 2.38 mmol), methyl 4-bromo-3-fluorobenzoate (665 mg, 2.856 mmol), 1,1′-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (292 mg, 0.358 mmol), potassium carbonate (2.38 ml, aq., 2M, 4.76 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 145° C. for 15 min. Aliquot indicated formation of the desired cpd. TLC (20% EtOAc/hex) indicated a bright purple spot @ Rf=0.4. Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. Related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=278.08; found=279.09 (M+1)+. irradiation at 145° C. for 15 min Crude mixture was dried/Na2SO4 then purified by flash chromatography (SiO2, Biotage 40+M cartridge) The column was eluted by a 0% to 20% EtOAc/hexanes mixture concentrated in vacuo