Triphenylphosphine → 5-Bromo-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one

HRID 920924ノート

反応式

HRID 920924 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][NH:39][C:40]2=[O:45].[N:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[CH2:56][CH2:57]O>C1COCC1.O>[Br:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[N:38][N:39]([CH2:57][CH2:56][C:47]1[CH:48]=[CH:49][C:50]3[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:46]=1)[C:40]2=[O:45]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866831365-Bromo-1,2-dihydrophthalazin-1-one

生成物 1

HCID 866831355-Bromo-2-[2-(quinolin-2-yl)ethyl]phthalazin-1(2H)-one収率 59.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of PPh3 (699 mg, 2.67 mmol) in THF (50 mL) and DIAD (198 mg, 0.98 mmol), 5-bromo-2H-phthalazin-1-one (300 mg, 1.33 mmol) and then 2-quinolin-2-yl-ethanol from example a1 (254 mg, 1.46 mmol) were added dropwise at 15° C. under nitrogen. The mixture was stirred at room temperature overnight. Water was added and the mixture was extracted with EtOAc. The organic phase was washed with HCl (1 N). The aqueous phase was basified and extracted with DCM. The organic phase was washed with a NaHCO3-solution, dried over Na2SO4, filtered and concentrated. The crude product was recrystallized from EA and dried to give the title compound as bright beige solid (300 mg, 59.2% yield).

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase was washed with HCl (1 N)
  3. extractionextracted with DCM
  4. washThe organic phase was washed with a NaHCO3-solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from EA
  9. customdried

出典と根拠

ORDレコード
ord-1d3ca820680a4a4bab930a749a5760c2
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

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