Dimethylformamide → Methyl 4-cyano-3-methoxybenzoate

Triphenylphosphine polymer bound (50 mg; 0.15 mmol; 0.15 eq.), palladium (II) acetate (15.04 mg; 0.07 mmol; 0.07 eq.) and DMF (3 mL) were first mixed, purged with N2 and let stirring at RT for 2 h. The vial was then opened, zinc cyanide (117.43 mg; 1 mmol; 1 eq.) and methyl 4-bromo-3-methoxybenzoate (COMBI-BLOCKS; CA-4192; 245.07 mg; 1 mmol; 1 eq.) were added and the resulting mixture was purged once more before heating at 140° C. for 50 min. The reaction mixture was then filtrated through a glass frit and the resin was washed with Et2O (3×10 mL). The combined organic solutions were washed with water (3×5 mL), once with NaCl sat. solution (10 mL) and then dried over magnesium sulfate. Evaporation of the solvent gave the title compound as a white solid (137 mg; 72%). 1H NMR (DMSO-d6, 300 MHz) δ 7.91 (d, J=7.9 Hz, 1H), 7.66-7.62 (m, 2H), 4 (s, 3H), 3.90 (s, 3H). LC/MS (Method A): 232.8 (M+ACN)+. GC/MS: 191. HPLC (Method A), Rt 3.14 min (purity: 99.3%).

1. custompurged with N2
2. customthe resulting mixture was purged once more
3. temperaturebefore heating at 140° C. for 50 min
4. filtrationThe reaction mixture was then filtrated through a glass frit
5. washthe resin was washed with Et2O (3×10 mL)
6. washThe combined organic solutions were washed with water (3×5 mL), once with NaCl sat. solution (10 mL)
7. dry with materialdried over magnesium sulfate
8. customEvaporation of the solvent

ORD record

ord-571a45edb9ca4630a1115718f5826202

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08202865B2