2-Pyridinecarboxaldehyde → HCID 89601195, compound

Temperature

0 °C

To a stirred solution of 2-(4-bromo-2,6-dichloro-phenyl)-3-methoxy-cyclopent-2-en-1-one (0.86 g, 2.56 mmol) in anhydrous tetrahydrofuran (17 ml) at 0°C. under an nitrogen atmosphere was added dropwise potassium hexamethyldisilazide (2.81 ml of a 1.0M solution in tetrahydrofuran, 2.81 mmol) over 10 minutes followed by dropwise addition of a solution of pyridine-2-carbaldehyde (0.268 ml, 2.81 mmol) in tetrahydrofuran (1 ml) over 5 minutes. The reaction was stirred at 0°C. for 10 minutes and then allowed to warm to room temperature over 1.5 hours. The reaction was quenched with saturated aqueous NH4Cl (25 ml) and extracted with EtOAc (3×25 ml). The combined organic extracts were washed with brine (15 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography over silica using an EtOAc/isohexane gradient to give the desired product (250 mg, 20%). 1H NMR (400 MHz, CDCl3) δ ppm 8.70 (d, 1H), 7.70 (dd, 1H), 7.55 (s, 2H), 7.45 (d, 1H), 7.40 (s, 1H), 7.25-7.20 (m, 1H), 4.05 (s, 2H), 3.95 (s, 3H).

1. temperatureto warm to room temperature over 1.5 hours
2. customThe reaction was quenched with saturated aqueous NH4Cl (25 ml)
3. extractionextracted with EtOAc (3×25 ml)
4. washThe combined organic extracts were washed with brine (15 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated to dryness under reduced pressure
8. customThe crude product was purified by flash chromatography over silica using an EtOAc/isohexane gradient

ORD record

ord-92437a3af74141568f66fffca84873b2

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09107415B2