Sodium Carbonate → HCID 21196371, compound

A mixture of 5-bromo-2-methoxybenzaldehyde (10.00 g, 1.82 mmol) and tetrakis (triphenylphosphine)palladium (O) (2.10 g, 1.82 mmol, 3.9 mol %) in DME (filtered through Al2O3) (50 ml) was stirred at RT for 0.25 h. Sodium carbonate (2M, 50 ml, 0.10 mol %) and diethyl (3-pyridyl)borane (6.817 g, 46.36 mmol) were added, the mixture heated to reflux for 5.5 h then allowed to stand at RT overnight. The dark brown reaction mixture was partitioned between water (50 ml) and Et2O (100 ml) and the organic layer separated and combined with two further Et2O extracts (1×50 ml, 1×25 ml). The organic phase was extracted with 2N hydrochloric acid (2×50 ml) then the aqueous extract was basified with 3M NaOH and extracted with Et2O (1×150 ml, 2×50 ml). The combined organic extract was washed with brine (50 ml), dried (Na2SO4), concentrated in vacuo then submitted to column chromatography [SiO2; Et2O] to furnish the title compound (3.318 g) as a pale yellow solid (Found: C, 73.40; H, 5.20; N, 6.44. C13H11NO2 requires C, 73.23; H, 5.20; N, 6.57%.).

1. temperaturethe mixture heated
2. temperatureto reflux for 5.5 h
3. waitto stand at RT overnight
4. customThe dark brown reaction mixture was partitioned between water (50 ml) and Et2O (100 ml)
5. customthe organic layer separated
6. extractionThe organic phase was extracted with 2N hydrochloric acid (2×50 ml)
7. extractionthe aqueous extract
8. extractionextracted with Et2O (1×150 ml, 2×50 ml)
9. extractionThe combined organic extract
10. washwas washed with brine (50 ml)
11. dry with materialdried (Na2SO4)
12. concentrationconcentrated in vacuo

ORD record

ord-4138f58b42e44536b17bfdb52e64e0f1

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245774B1