Diisopropylamine → HCID 69082971, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence