Potassium Phosphate, Tribasic → HCID 10134791、化合物

HRID 586283ノート

反応式

HRID 586283 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][N:12]=1.Br[C:20]1[N:24]2[N:25]=[CH:26][C:27]([C:29]([F:32])([CH3:31])[CH3:30])=[N:28][C:23]2=[N:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C)C=O>[F:17][C:16]1[C:11]([C:3]2[CH:4]=[C:5]([C:20]3[N:24]4[N:25]=[CH:26][C:27]([C:29]([F:32])([CH3:30])[CH3:31])=[N:28][C:23]4=[N:22][CH:21]=3)[CH:6]=[CH:7][C:2]=2[F:1])=[N:12][CH:13]=[C:14]([F:18])[CH:15]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 11459593HCID 11459593、化合物HCID 116374193-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acid

生成物 1

HCID 10134791HCID 10134791、化合物

試薬・触媒・溶媒 2

HCID 53485975CID 53485975触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To 4-fluoro-3-(3,5-difluoropyridin-2-yl)phenylboronic acid (0.08 g) and 7-bromo-3-(1-fluoro-1-methylethyl)imidazo[1,2-b][1,2,4]triazine (0.06 g, 0.23 mmol) was added dry potassium phosphate (0.3 g), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.04 g) and dry N,N-dimethylformamide (3 ml). The mixture was degassed, then stirred for 24 h at 80° C. under an atmosphere of dry nitrogen. The reaction was cooled to ambient temperature, and the solvent was stripped at reduced pressure. The residue was boiled with toluene (25 ml), and filtered hot. The filtrate was evaporated and the residue subjected to preparative thin layer chromatography (silica gel; 2.5% MeOH/CH2Cl2). The recovered product was crystallised from hot toluene/isohexane to afford the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 1.80 (6H, d, J 22.1 Hz), 7.60 (1H, dd, J 8.8, 9.8 Hz), 8.18 (1H, m), 8.32 (1H, m), 8.37 (1H, m), 8.59 (1H, s), 8.74 (1H, d, J 2.3 Hz), 9.03 (1H, s); MS (ES+) m/z 388 [M+H]+.

後処理

  1. customThe mixture was degassed
  2. temperatureThe reaction was cooled to ambient temperature
  3. filtrationfiltered hot
  4. customThe filtrate was evaporated
  5. customThe recovered product was crystallised from hot toluene/isohexane

出典と根拠

ORDレコード
ord-0516099f8e984059954da8a46b13b9a1
出典データセット
uspto-grants-2005_08
特許番号
US06936608B2

反応ノート

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