تفاعل #45378

معادلة التفاعل

(6-bromopyridin-2-yl)methanol

phthalimide

triphenylphosphine

1,1′-(azodicarbonyl)-dipiperidine

TFA

TFA

→

2-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

المذيبات

MeOH

tetrahydrofuran

H2O

H2O

methanol

MeOH

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe precipitate was collected by vacuum filtration
2. 2
   غسيلwashed with tetrahydrofuran
3. 3
   تركيزThe filtrate was concentrated under reduced pressure
4. 4
   أخرىthe solid residue was triturated with methanol with sonication
5. 5
   ترشيحA214.1 was collected by vacuum filtration
6. 6
   أخرىwas dried well
7. 7
   أخرىto give 24.1 g as a white solid

الإجراء التجريبي

A mixture of commercially available (6-bromopyridin-2-yl)methanol (20.0 g, 0.106 mol), phthalimide (20.4 g, 0.138 mol), and triphenylphosphine (36.2 g, 0.138 mol), and 1,1′-(azodicarbonyl)-dipiperidine (34.8 g, 0.138 mol) in anhydrous tetrahydrofuran (1 L) was stirred at room temperature overnight. The precipitate was collected by vacuum filtration and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure, and the solid residue was triturated with methanol with sonication. A214.1 was collected by vacuum filtration and was dried well to give 24.1 g as a white solid. The filtrate still contained significant product which could be isolated as a second crop with methanol trituration. The compound had an HPLC retention time=2.32 min. (Column: Chromolith SpeedROD 4.6×50 mm—4 min.; Solvent A=10% MeOH, 90% H2O, and 0.1% TFA; Solvent B=90% MeOH, 10% H2O, and 0.1% TFA) and a LC/MS M+1=317.15 and 319.15.

المصدر