Sodium Carbonate → 2-[1-(3-pyridyl)pyrazol-4-yl]-6,7-dihydro-5H-quinolin-8-one

HRID 1478533ノート

反応式

HRID 1478533 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[O:12])[C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[N:23][N:24]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:25]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C(OCC)(=O)C>[N:28]1[CH:29]=[CH:30][CH:31]=[C:26]([N:24]2[CH:25]=[C:21]([C:2]3[CH:11]=[CH:10][C:9]4[CH2:8][CH2:7][CH2:6][C:5](=[O:12])[C:4]=4[N:3]=3)[CH:22]=[N:23]2)[CH:27]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 146801122-Chloro-5,6,7,8-tetrahydroquinolin-8-oneHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine

生成物 1

HCID 900442112-[1-(3-pyridyl)pyrazol-4-yl]-6,7-dihydro-5H-quinolin-8-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-chloro-6,7-dihydro-8(5H)-quinolinone (1.14 g, 6.3 mmol, prepared as described in J. Org. Chem. 1990, 55, 4789) and 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-pyridine (1.7 g, 6.3 mmol, WO 2012/000896), sodium carbonate (3.15 g, 29.6 mmol) in a mixture of acetonitrile (50 ml) and water (30 ml) was purged with argon for 10 min. To this solution was added Pd[P(Ph)3]4 (270 mg, 0.23 mmol) and the solution was heated at 80° C. overnight. The reaction mixture was diluted with ethyl acetate and the water phase was separated. The organic phase was washed with brine and dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was crystallized in isopropanol/petrol ether (1:1) to give two crops of the title product as a beige solid.

後処理

  1. customwas purged with argon for 10 min
  2. customthe water phase was separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized in isopropanol/petrol ether (1:1)

出典と根拠

ORDレコード
ord-0be3dd42fa7f427188fb889518ab14f4
出典データセット
uspto-grants-2016_08
特許番号
US09403845B2

反応ノート

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