Potassium Fluoride → HCID 68958235、化合物

HRID 269389ノート

反応式

HRID 269389 の反応式
Cl[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

8

反応物 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 2776266Benzo[b]furan-2-boronic acidHCID 134045925-Chloro-8-methoxyquinoline

生成物 1

HCID 68958235HCID 68958235、化合物収率 62.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 5-chloro-8-methoxy-quinoline (0.330 g, 1.70 mmol) in THF (2 mL) at room temperature was added benzofuran-2-boronic acid (0.413 g, 2.55 mmol) followed by KF (0.296 mL, 5.10 mmol), Pd(OAc)2 (0.0382 g, 0.170 mmol), and 2-(di-tert-butyl phosphino)biphenyl (0.101 g, 0.340 mmol). The reaction mixture was stirred at room temperature for 18 hours and then diluted with EtOAc (200 mL). The organic layer was washed with H2O (20 mL) and brine (20 mL) then dried (Na2SO4). After concentration, the residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether) to afford the product (0.291 g, 62%) as a solid. Mass spectrum (+ESI, [M+H]+) m/z 276. 1H NMR (500 MHz, DMSO-d6): δ 8.94 (d, 1H, J=2.2 Hz), 8.83 (d, 1H, J=9.4 Hz), 7.99 (d, 1H, J=8.6 Hz), 7.66-7.77 (m, 3H), 7.27-7.41 (m, 4H), and 4.6 ppm (s, 3H).

後処理

  1. washThe organic layer was washed with H2O (20 mL) and brine (20 mL)
  2. dry with materialthen dried (Na2SO4)
  3. concentrationAfter concentration
  4. customthe residue was purified on a Biotage Flash 40 apparatus (30-70% EtOAc:petroleum ether)

出典と根拠

ORDレコード
ord-766455aae57e44d0a4de7d78f6ab2011
出典データセット
uspto-grants-2008_11
特許番号
US07446201B2

反応ノート

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