Sodium Carbonate → 3-Methyl-2-trimethylsilanyl-1H-indole-5-carbonitrile

Temperature

100 °C

1-(Trimethylsilyl)propyne (2.23 ml, 1.68 g, 15.0 mmol), 4-amino-3-iodobenzonitrile (3.33 g, 13.65 mmol), lithium chloride (606 mg, 14.3 mmol) and sodium carbonate (4.35 g, 40.95 mmol) were added successively to abs. dimethylformamide (60 ml) under argon. Pd(dppf)Cl2 (1.116 g, 1.365 mmol) was added to this mixture and the reaction mixture was heated at 100° C. with exclusion of moisture for 6 h and then stirred at room temperature for 16 h. For working up of the mixture, water (150 ml) and ethyl acetate (300 ml) was added and the mixture was stirred for 10 min. After separation of the phases, the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with saturated sodium chloride solution (3×100 ml), dried and concentrated. The residue was a brown oil (5.5 g) which, apart from 3-methyl-2-trimethylsilanyl-1H-indole-5-carbonitrile, contained traces of the isomer 2-methyl-3-trimethylsilanyl-1H-indole-5-carbonitrile and DMF.

1. additionwas added
2. stirringthe mixture was stirred for 10 min
3. customAfter separation of the phases
4. extractionthe aqueous phase was extracted with ethyl acetate (3×100 ml)
5. washThe combined organic phases were washed with saturated sodium chloride solution (3×100 ml)
6. customdried
7. concentrationconcentrated

ORD record

ord-64a63c0078ea43af89051c3d46847bfe

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138187B2