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

HRID 17100

反応式

HRID 17100 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒3 回HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

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.

後処理

  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

出典と根拠

ORDレコード
ord-b3467d2092bb4e8c87455c945af69572
出典データセット
uspto-grants-2010_06
特許番号
US07737279B2

関連ノート

読み込み中…