Potassium Acetate → 5-Methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-quinolin-8-ylpyridazin-4(1H)-one

HRID 1895315ノート

反応式

HRID 1895315 の反応式
Br[C:2]1[C:7](=[O:8])[C:6]([O:9][CH3:10])=[CH:5][N:4]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[N:19]=[CH:18][CH:17]=[CH:16]3)[N:3]=1.[C:21]1([N:27]2[C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][CH:29]=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CC([O-])=O.[K+]>C(O)CCC.O>[CH3:10][O:9][C:6]1[C:7](=[O:8])[C:2]([C:31]2[N:27]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:28]=[CH:29][CH:30]=2)=[N:3][N:4]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:20]=2[N:19]=[CH:18][CH:17]=[CH:16]3)[CH:5]=1

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 580723671-Phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 594361483-bromo-5-methoxy-1-quinolin-8-ylpyridazin-4(1H)-one

生成物 1

HCID 580721885-Methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-1-quinolin-8-ylpyridazin-4(1H)-one収率 81.5%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒2 回

実験手順

A mixture of 3-bromo-5-methoxy-1-quinolin-8-ylpyridazin-4(1H)-one (70 mg, 0.217 mmol), 1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (88.1 mg, 0.326 mmol), KOAc (42.6 mg, 0.434 mmol) and PdCl2{P(t-Bu)2(Ph-p-NMe2)}2 (7.7 mg, 0.0109 mmol) in BuOH (1.1 mL) and water (0.1 mL) was heated to reflux for 16 h under Ar atmosphere. The mixture was diluted with water, extracted with AcOEt, washed with saturated NaHCO3 aqueous solution, dried over Na2SO4, filtered, concentrated in vacuo, purified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100 and AcOEt/MeOH=100/0 to 70/30) and recrystallized with AcOEt/hexane to yield the title compound (69.9 mg, 81% yield) as a white solid: mp 189-192° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.76 (3H, s), 6.98 (1H, s), 7.31-7.49 (6H, m), 7.58-7.73 (2H, m), 7.78 (1H, d, J=1.9 Hz), 8.14 (1H, d, J=8.3 Hz), 8.54 (1H, d, J=7.9 Hz), 8.67 (1H, s), 8.99 (1H, d, J=4.1 Hz). Anal. Calcd for C23H17N5O2: C, 69.86; H, 4.33; N, 17.71. Found: C, 69.61; H, 4.37; N, 17.57.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 16 h under Ar atmosphere
  3. extractionextracted with AcOEt
  4. washwashed with saturated NaHCO3 aqueous solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100 and AcOEt/MeOH=100/0 to 70/30)
  9. customrecrystallized with AcOEt/hexane

出典と根拠

ORDレコード
ord-3f0dab8ceef448e5af3387eeed5badb3
出典データセット
uspto-grants-2013_08
特許番号
US08513251B2

反応ノート

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