반응 #45378

반응 방정식

(6-bromopyridin-2-yl)methanol

phthalimide

triphenylphosphine

1,1′-(azodicarbonyl)-dipiperidine

TFA

TFA

→

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

용매

MeOH

tetrahydrofuran

H2O

H2O

methanol

MeOH

반응 조건

후처리

1. 1
   여과The precipitate was collected by vacuum filtration
2. 2
   세척washed with tetrahydrofuran
3. 3
   농축The filtrate was concentrated under reduced pressure
4. 4
   기타the solid residue was triturated with methanol with sonication
5. 5
   여과A214.1 was collected by vacuum filtration
6. 6
   기타was dried well
7. 7
   기타to give 24.1 g as a white solid

실험 절차

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.

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