Sodium Carbonate → HCID 21083623, compound

HRID 347703Notes

Reaction equation

HRID 347703 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11](=[O:22])[N:12]([C:14]3[C:19]([C:20]#[N:21])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:13]=2)OC1.Br[C:25]1[N:29]2[N:30]=[CH:31][C:32]([C:34]([OH:37])([CH3:36])[CH3:35])=[N:33][C:28]2=[N:27][CH:26]=1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.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>[OH:37][C:34]([C:32]1[CH:31]=[N:30][N:29]2[C:25]([C:8]3[CH:9]=[CH:10][C:11](=[O:22])[N:12]([C:14]4[C:19]([C:20]#[N:21])=[CH:18][CH:17]=[CH:16][N:15]=4)[CH:13]=3)=[CH:26][N:27]=[C:28]2[N:33]=1)([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 21083625HCID 21083625, compound

Product 1

HCID 21083623HCID 21083623, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a degassed mixture of 5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-oxo-2H-[1,2′]bipyridinyl-3′-cabonitrile (from step f), 2-(7-bromo-imidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (from step d) (0.23 g), dry 1,4-dioxane (5 ml), and 2 M aqueous sodium carbonate (3 ml), was added tetrakis(triphenylphosphine)palladium(0) (0.12 g). The mixture was heated at 95° C. under a nitrogen atmosphere for 24 h. After cooling to 25° C., the reaction was diluted with ethyl acetate, and the organic phase separated. The solvent was evaporated at reduced pressure and the residue purified by chromatography (silica gel, 5% MeOH/CH2Cl2) to give the title compound, crystallised from hot isopropanol as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.98 (1H, s), 8.97 (1H, d, J 2.0), 8.62–8.68 (2H, m), 8.40 (1H, s), 8.32 (1H, dd, J 2.7, 9.8), 7.85 (1H, dd, J 5.1, 7.8), 6.83 (1H, d, J 9.8), 5.75 (1H, s), 1.54 (6H, s); MS (ES+) m/z 374 [M+H]+.

Workup

  1. temperatureAfter cooling to 25° C.
  2. customthe organic phase separated
  3. customThe solvent was evaporated at reduced pressure
  4. customthe residue purified by chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-17ae2df0a7074c54aa97780dcab68172
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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