Phenol → HCID 86657872, compound

Temperature

150 °C

A mixture of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (3.29 g, 9.23 mmol), phenol (1.04 g, 11.08 mmol), K3PO4 (3.92 g, 18.46 mmol), [2′-(di-tert-butyl-phosphanyl)-biphenyl-2-yl]-dimethyl-amine (0.157 g, 0.46 mmol), Pd(OAc)2 (0.103 g, 0.46 mmol) and degassed toluene (50 mL) was stirred under nitrogen in a sealed tube at 150° C. overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by SiO2 column chromatography (0-30% EtOAc/hexanes) to afford 2.09 g (61%) of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a beige solid.

1. customdegassed toluene (50 mL)
2. temperatureThe reaction mixture was cooled to room temperature
3. custompartitioned between ethyl acetate and water
4. extractionThe aqueous layer was extracted with ethyl acetate
5. dry with materialthe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by SiO2 column chromatography (0-30% EtOAc/hexanes)

ORD record

ord-bf5326cfce7f4475bf399bbdda93b020

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2