Sodium Carbonate → HCID 10271398, compound

HRID 586280Notes

Reaction equation

HRID 586280 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]([OH:32])([CH3:31])[CH3:30])=[N:28][C:23]2=[N:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>[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]([OH: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 10340Sodium CarbonateHCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 116374193-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acid

Product 1

HCID 10271398HCID 10271398, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 4-fluoro-3-(3,5-difluoropyridin-2-yl)phenylboronic acid (0.40 g) and 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (0.391 g) was added tetrahydrofuran (5 ml) and 2 N aqueous sodium carbonate (1.5 ml). Tetrakis(triphenylphosphine)palladium(0) (0.07 g) was added, the mixture was thoroughly degassed with nitrogen, and then stirred at 60° C. for 24 h. On cooling to room temperature, the reaction was partitioned between water and ethyl acetate. The organic extracts were evaporated, and the residue was subjected to chromatography (silica gel, 35% EtOAc/CH2Cl2). The product was crystallised from dichloromethane/isohexane, and the resulting pale yellow solid was collected by filtration and dried in vacuo at 60° C. to afford the title compound: 1H NMR (400 MHz, DMSO-d6) δ 1.56 (6H, s), 5.76 (1H, s), 7.58 (1H, dd, J 8.8, 10 Hz), 8.17 (1H, m), 8.29-8.36 (2H, m), 8.48 (1H, s), 8.74 (1H, d, J 2.3 Hz), 9.02 (1H, s); MS (ES+) m/z 386 [M+H]+.

Workup

  1. customthe mixture was thoroughly degassed with nitrogen
  2. temperatureOn cooling to room temperature
  3. customthe reaction was partitioned between water and ethyl acetate
  4. customThe organic extracts were evaporated
  5. customThe product was crystallised from dichloromethane/isohexane
  6. filtrationthe resulting pale yellow solid was collected by filtration
  7. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-43c840067e944aa19047ccc030ae4f42
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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