Diisopropylamine → HCID 69082971, compound

Temperature

-30 °C

To a solution of diisopropylamine (8.98 mL, 63 mmol) in tetrahedrofuran (22.5 mL) in 1 L flask at −78° C. was added n-butyllithium (25.2 mL, 2.5M in hexane, 63.0 mmol) dropwise. The reaction was allowed to gradually warm in the bath to −30° C., and held there for 5 minutes. It was re-cooled to −78° C. and treated with solid 2-(5-bromopyridin-3-yl)acetic acid (6.80 g, 31.5 mmol) and tetahydrofuran (78 mL). The ice bath was removed and stirring continued for 1.5 h. The reaction was again cooled to 0° C., and treated with a solution of 4-fluorobenzaldehyde (3.38 mL, 31.5 mmol) in tetrahydrofuran (22.5 mL). The reaction was allowed to gradually warm to room temperature overnight. The reaction solution, after removal of the solid by filtration, was acidified with citric acid to pH ca. 4. It was extracted with diethyl ether and concentrated. The resulting residue was dried three times with toluene and the crude product (ca. 10.1 g) was used in the next reaction without further purification. Mass spec.: 340.9 (MH)+.

1. temperatureIt was re-cooled to −78° C.
2. customThe ice bath was removed
3. waitcontinued for 1.5 h
4. temperatureThe reaction was again cooled to 0° C.
5. temperatureto gradually warm to room temperature overnight
6. customThe reaction solution, after removal of the solid
7. filtrationby filtration
8. extractionIt was extracted with diethyl ether
9. concentrationconcentrated
10. dry with materialThe resulting residue was dried three times with toluene
11. customthe crude product (ca. 10.1 g) was used in the next reaction without further purification

ORD record

ord-28336c701ea74cc4ab9c3a4821fdc143

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691821B2