Benzene, 1-bromo-4-ethynyl- → HCID 67336193, compound

Temperature

0 °C

To a solution of the intermediate from step A (2.1 g, 11.6 mmol) in anhydrous THF (80 mL) cooled to −78° C. under a N2 atmosphere was added LHMDS (1.0 M solution in THF, 11.6 mL). After 5 minutes a solution of 3,5-dichloro-N-methoxy-N-methyl benzamide (2.71 g, 11.6 mmol) in THF (20 mL) was added to the reaction. The reaction was slowly warmed to 0° C. over 30 minutes and then quenched with saturated NH4Cl solution. The resulting bi-phasic mixture was extracted with EtOAc (3×). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 1:10 ethyl acetate-hexanes to give the title compound as a bright yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.07 (d, J=1.8 Hz, 2H), 7.66 (t, J=1.9 Hz, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.6 (d, J=8.7 Hz, 2H).

1. customquenched with saturated NH4Cl solution
2. extractionThe resulting bi-phasic mixture was extracted with EtOAc (3×)
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography

ORD record

ord-692e92a86b484e50b92006beb198843e

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989475B2