Sodium Carbonate → 2-Chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile

Temperature

100 °C

To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), 3-bromo-5-fluoroisonicotinaldehyde (204 mg, 1.00 mmol) and PdCl2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2CO3 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4Cl solution. After extraction and separation, the combined extracts were concentrated and purified by SNAP10 g (10% MeOH/DCM 0-15% gradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18%) as a white solid; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15 min. 1H-NMR (CDCl3, 400 MHz) δ 7.33 (dd, J=8.0, 1.6 Hz, 1H), 7.50 (d, J=1.6 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 8.49 (s, 1H), 8.78 (d, J=1.2 Hz, 1H), 10.27 (s, 1H).

1. temperatureAfter letting cool to room temperature
2. customsolvent was removed in vacuo
3. dissolutionThe resulting residue was dissolved in DCM
4. extractionAfter extraction and separation
5. concentrationthe combined extracts were concentrated
6. custompurified by SNAP10 g (10% MeOH/DCM 0-15% gradient)

ORD record

ord-5060bd4428a94798a8e2c37274ca53e6

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519134B2