Sodium Hydroxide → HCID 60197771, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-methyl 3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylate (120 mg, 0.34 mmol, 1.00 equiv) in methanol (15 mL) was added a solution of sodium hydroxide (136 mg, 3.40 mmol, 9.97 equiv) in water (2 mL). The resulting solution was stirred for 2 h at 50° C. in an oil bath, concentrated in vacuo, and diluted with 20 mL of water. The pH value was adjusted to 4-5 with HCl (1M). The resulting solids were collected by filtration, and purified by Prep-HPLC with the following conditions (1#-Waters 2767-2): Column, SunFire Prep C18, 19*150 mm Sum; mobile phase, water with 0.05% TFA and CH3CN (50% CH3CN up to 60% in 8 min, hold 60% in 1 min, up to 100% in 0.1 min, hold 100% in 0.9 min); Detector, UV 220&254 nm. This resulted in 50 mg (43%) of (E)-3-(5,6-bis(4-fluorophenyl)pyrazin-2-yl)acrylic acid as a white solid.

Provenance & Evidence