Triethylamine → Tert-butyl {4-[(3-aminophenyl)ethynyl]pyridin-2-yl}carbamate

Temperature

70 °C

tert-Butyl (4-bromopyridin-2-yl)carbamate (1.935 g, 7.09 mmol), copper(I) iodide (0.67 g, 3.5 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.20 g, 0.28 mmol) were stirred in tetrahydrofuran (22 mL) with triethylamine (1.09 mL, 7.82 mmol) under N2 at rt. 3-Ethynylaniline (0.815 mL, 7.79 mmol) was added and the mixture was heated at 70° C. for 2 hours and only very little product was observed. Thus more 3-ethynylaniline (0.41 mL, 3.9 mmol) was added and the mixture was heated at 70° C. over the weekend. The reaction mixture was filtered and concentrated to give a brown residue, which was purified by silica gel column chromatography to give the desired product (340 mg, 16%). LCMS for C18H20N3O2 (M+H)+: m/z=310.1

1. temperaturethe mixture was heated at 70° C. over the weekend
2. filtrationThe reaction mixture was filtered
3. concentrationconcentrated
4. customto give a brown residue, which
5. customwas purified by silica gel column chromatography

ORD record

ord-d7029913eeb048a697aa56da42fb49b3

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2