反応 #45378

反応方程式

(6-bromopyridin-2-yl)methanol

phthalimide

triphenylphosphine

1,1′-(azodicarbonyl)-dipiperidine

TFA

TFA

→

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

溶媒

MeOH

tetrahydrofuran

H2O

H2O

methanol

MeOH

反応条件

後処理

1. 1
   ろ過The precipitate was collected by vacuum filtration
2. 2
   洗浄washed with tetrahydrofuran
3. 3
   濃縮The filtrate was concentrated under reduced pressure
4. 4
   その他the solid residue was triturated with methanol with sonication
5. 5
   ろ過A214.1 was collected by vacuum filtration
6. 6
   その他was dried well
7. 7
   その他to give 24.1 g as a white solid

実験手順

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.

出典