Potassium Phosphate, Tribasic → HCID 10134791, 화합물

HRID 586283노트

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HRID 586283 반응식
[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

참가 물질

6

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

생성물 1

HCID 10134791HCID 10134791, 화합물

시약·촉매·용매 2

HCID 53485975CID 53485975촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-0516099f8e984059954da8a46b13b9a1
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936608B2

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