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

HRID 17100

Reaktionsgleichung

Reaktionsgleichung von HRID 17100
[Br:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(O)(C(F)(F)F)=O>O1CCCC1.O.CO>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 6422Trifluoroacetic acid2×HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 3517811(6-Bromopyridin-2-yl)methanol

Produkt 1

HCID 221764462-((6-Bromopyridin-2-yl)methyl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel3×HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe solid residue was triturated with methanol with sonication
  5. filtrationA214.1 was collected by vacuum filtration
  6. customwas dried well
  7. customto give 24.1 g as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-b3467d2092bb4e8c87455c945af69572
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737279B2

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