Phthalic Anhydride → 2-((5-Bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 587717ノート

反応式

HRID 587717 の反応式
Cl.[Br:2][C:3]1[CH:4]=[C:5]([Cl:11])[C:6]([CH2:9][NH2:10])=[N:7][CH:8]=1.[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([Cl:11])[C:6]([CH2:9][N:10]2[C:15](=[O:16])[C:14]3[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:17])=[N:7][CH:8]=1

参加物

4

反応物 2

HCID 6811Phthalic AnhydrideHCID 71138342(5-Bromo-3-chloropyridin-2-yl)methanamine hydrochloride

生成物 1

HCID 711385752-((5-Bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dione収率 65%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a stirred solution of (5-bromo-3-chloropyridin-2-yl)methanamine hydrochloride (0.3 g, 1.4 mmol) in toluene (40 mL) was added TEA (0.41 g, 4.08 mmol) and phthalic anhydride (0.24 g, 1.63 mmol), and the reaction mixture was heated at reflux for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with EtOAc. The combined EtOAc layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (20-30% EtOAc in hexane) to afford the title compound as a white solid (0.25 g, 65%): 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.45 (s, 1H), 7.88 (m, 2H), 7.74 (m, 2H), 4.56 (m, 2H); ESIMS m/z 349 ([M−H]−); IR (thin film) 3307, 1665, 1114, 813 cm−1.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAc
  6. washThe combined EtOAc layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (20-30% EtOAc in hexane)

出典と根拠

ORDレコード
ord-00b380baba424b8dab3ad5111e180502
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

読み込み中…