Benzoic acid, 5-chloro-2-iodo-, ethyl ester

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 degassed mixture of ethyl 5-chloro-2-iodobenzoate (0.621 g, 2.00 mmol), Pd(PPh3)4 (0.116 mg, 0.1 mmol), quinolin-6-ylboronic acid (0.381 g, 2.2 mmol), K2CO3 (0.553 g, 4.0 mmol), dimethoxyethane (20 mL), and water (5 mL) was heated under reflux overnight. Solvents were removed under reduced pressure. The residue was diluted with sat'd NH4Cl (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried (MgSO4), concentrated in vacuo and purified by chromatography to afford ethyl 5-chloro-2-(quinolin-6-yl)benzoate (0.244 g, 39% yield) as a colorless oil. MS (ESI) m/z: 312.0 (M+H+). was heated under reflux overnight Solvents were removed under reduced pressure The residue was diluted with sat'd NH4Cl (15 mL) extracted with EtOAc (3×30 mL) The combined organic layers were dried (MgSO4) concentrated in vacuo purified by chromatography

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

Procedure: A degassed mixture of ethyl 5-chloro-2-iodobenzoate (0.621 g, 2.00 mmol), Pd(PPh3)4 (0.116 mg, 0.1 mmol), dimethoxyethane (20 mL), phenylboronic acid (0.268 g, 2.2 mmol), K2CO3 (0.829 g, 6.0 mmol), and water (5 mL) was heated under reflux for 6 h. Solvent was removed under reduced pressure. The residue was diluted with sat. NH4Cl (15 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by chromatography to afford ethyl 5-chloro-2-phenylbenzoate (0.473 g, 91%) as colorless oil. MS (ESI) m/z: 261.0 (M+H+). was heated under reflux for 6 h Solvent was removed under reduced pressure The residue was diluted with sat. NH4Cl (15 mL) extracted with EtOAc (2×30 mL) The combined organic layers were dried (MgSO4) concentrated The crude product was purified by chromatography

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

Procedure: A degassed mixture of ethyl 5-chloro-2-iodobenzoate (0.621 g, 2.00 mmol), Pd(PPh3)4 (0.116 mg, 0.1 mmol), quinolin-6-ylboronic acid (0.381 g, 2.2 mmol), K2CO3 (0.553 g, 4.0 mmol), dimethoxyethane (20 mL), and water (5 mL) was heated under reflux overnight. Solvents were removed under reduced pressure. The residue was diluted with sat'd NH4Cl (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried (MgSO4), concentrated in vacuo and purified by chromatography to afford ethyl 5-chloro-2-(quinolin-6-yl)benzoate (0.244 g, 39% yield) as a colorless oil. MS (ESI) m/z: 312.0 (M+H+). was heated under reflux overnight Solvents were removed under reduced pressure The residue was diluted with sat'd NH4Cl (15 mL) extracted with EtOAc (3×30 mL) The combined organic layers were dried (MgSO4) concentrated in vacuo purified by chromatography