Sodium Carbonate → 5-(3,5-dichlorophenyl)-1H-indole-2-carboxylic acid ethyl ester

To a stirred solution of 5-bromo-3-chloro-1H-indole-2-carboxylic acid ethyl ester (500 mg, 1.86 mmol) and 3,5-dichlorophenyl boronic acid (530 mg, 2.78 mmol) in a mixture of MeCN (26 mL) and i-PrOH (3.3 mL) at room temperature under argon, was added Pd(OAc)2 (12 mg, 0.05 mmol), Ph3P (40 mg, 0.15 mmol) and Na2CO3 (2M aq., 16 mL) and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature the reaction was diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with water, brine and dried (MgSO4). Solvent removal and purification by chromatography afforded the sub-title compound (430 mg, 69%).

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 3 h
3. extractionextracted with EtOAc (3×30 mL)
4. washThe combined organic extracts were washed with water, brine
5. dry with materialdried (MgSO4)
6. customSolvent removal and purification by chromatography

ORD record

ord-355bf65a6dc247d8a6a2db493828223c

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07705023B2