Dimethylformamide → HCID 59428624, compound

Temperature

-15 °C

A 250-mL argon-purged round-bottomed flask equipped with a magnetic stirrer is charged with 4-Bromo-1H-pyrrolo[2,3-b]pyridine (0.70 g, 3.55 mmol) and DMF (25 mL) and the solution is cooled to −15° C. A 60% dispersion of sodium hydride in mineral oil (183 mg, 4.58 mmol) is then added and the reaction stirred at −15° C. for 25 min. The reaction is then charged with 4-picolylchloride hydrochloride (376 mg, 2.29 mmol) and stirred at −15° C. for a further 5 min. After such time the cooling bath is removed and the reaction is stirred for 30 min at ambient temperature. Additional 4-picolylchloride hydrochloride (117 mg, 0.71 mmol) and a 60% dispersion of sodium hydride in mineral oil (28 mg, 0.71 mmol) are then added and the reaction is stirred at ambient temperature for a further 30 min. The reaction is then poured into ethyl acetate (100 mL) and the mixture is washed with 3% aqueous sodium bicarbonate (1×100 mL), water (2×100 mL) and brine (1×100 mL). The organic layer is separated, dried over sodium sulfate and concentrated in vacuo to provide a residue, which is then purified by flash chromatography to afford 1b as a yellow solid.

1. customA 250-mL argon-purged round-bottomed flask
2. customequipped with a magnetic stirrer
3. stirringstirred at −15° C. for a further 5 min
4. customAfter such time the cooling bath is removed
5. stirringthe reaction is stirred for 30 min at ambient temperature
6. stirringthe reaction is stirred at ambient temperature for a further 30 min
7. washthe mixture is washed with 3% aqueous sodium bicarbonate (1×100 mL), water (2×100 mL) and brine (1×100 mL)
8. customThe organic layer is separated
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customto provide a residue, which
12. customis then purified by flash chromatography

ORD record

ord-1054a9c2a6ff4e3da9c104968c7b198f

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07777040B2