Potassium Phosphate, Tribasic → HCID 10134791, compound

HRID 586283Notes

Reaction equation

HRID 586283 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 10134791HCID 10134791, compound

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-0516099f8e984059954da8a46b13b9a1
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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