hexylboronic acid

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of Molander, et. al. (J. Org. Chem. 2009, 74, 3636), a suspension of 5-bromo-2-formylfuran (695 mg, 3.97 mmol), hexylboronic acid (775 mg, 5.96 mmol), potassium carbonate (1.65 g, 11.91 mmol), palladium(II) acetate (18 mg, 0.079 mmol) and RuPhos (74 mg, 0.16 mmol) in 9:1 toluene/water (22 mL) in a pressure-relief vial under argon was heated in a 120° C. bath for 18 h. After cooling to room temperature, the tion mixture was diluted with water (25 mL) and organics extracted with ether (3×50 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (10% ethyl acetate in hexanes) to give 5-hexyl-2-formylfuran (665 mg, 93%) as a clear oil. Used without further characterization. After cooling to room temperature organics extracted with ether (3×50 mL) dried with magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel (10% ethyl acetate in hexanes)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate. The mixture was purged with nitrogen The reaction was sealed The mixture was cooled filtered through celite rinsing with excess CH2Cl2 The filtrate was concentrated in vacuo The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate. The mixture was purged with nitrogen The reaction was sealed The mixture was cooled filtered through celite rinsing with excess CH2Cl2 The filtrate was concentrated in vacuo The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)

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

Procedure: Similar procedure as described in example 46d was used, starting from 4-chloro-3-cyano-quinoline-6-carboxylic acid ethyl ester (example 46c), n-hexylboronic acid, sodium carbonate and POPd to give 3-cyano-4-hexyl-quinoline-6-carboxylic acid ethyl ester as a clear oil. LC-MS m/e 311 (MH+).

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the method of Molander, et. al. (J. Org. Chem. 2009, 74, 3636), a suspension of 5-bromo-2-formylfuran (695 mg, 3.97 mmol), hexylboronic acid (775 mg, 5.96 mmol), potassium carbonate (1.65 g, 11.91 mmol), palladium(II) acetate (18 mg, 0.079 mmol) and RuPhos (74 mg, 0.16 mmol) in 9:1 toluene/water (22 mL) in a pressure-relief vial under argon was heated in a 120° C. bath for 18 h. After cooling to room temperature, the tion mixture was diluted with water (25 mL) and organics extracted with ether (3×50 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by chromatography on silica gel (10% ethyl acetate in hexanes) to give 5-hexyl-2-formylfuran (665 mg, 93%) as a clear oil. Used without further characterization. After cooling to room temperature organics extracted with ether (3×50 mL) dried with magnesium sulfate filtered concentrated The crude product was purified by chromatography on silica gel (10% ethyl acetate in hexanes)

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate. The mixture was purged with nitrogen The reaction was sealed The mixture was cooled filtered through celite rinsing with excess CH2Cl2 The filtrate was concentrated in vacuo The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)