Sodium Carbonate → HCID 10156337, compound

HRID 586305Notes

Reaction equation

HRID 586305 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B2OCC(C)(C)CO2)=[CH:18][C:17]=1[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[N:6]3[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:18][C:17]=1[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 22329524HCID 22329524, compound

Product 1

HCID 10156337HCID 10156337, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.05 g, 0.19 mmol), 3-[2-chloro-5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)phenyl]pyridine (84 mg, 0.28 mmol) and 2 M Na2CO3 (0.28 ml) in 1,2-dimethoxyethane (2 ml) was degassed for 10 min with a stream of nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.011 g) was added and the mixture was stirred under nitrogen at 80° C. for 12 h. After allowing to cool to ambient temperature, the mixture was diluted with ethyl acetate then partitioned between water (100 ml) and ethyl acetate (100 ml). The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2), to give 75 mg (61%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.42-7.45 (1H, m), 7.71 (1H, d, J 8.6 Hz), 7.86-7.89 (1H, m), 8.08 (1H, dd, J 8.6, 2.5 Hz), 8.14 (1H, d, J 2.5 Hz), 8.64 (1H, s), 8.70 (1H, dd, J 4.9, 2.3 Hz), 8.68 (1H, s), 8.82 (1H, dd, J 2.3, 1.0 Hz); MS (ES+) m/z 376.

Workup

  1. customwas degassed for 10 min with a stream of nitrogen
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.011 g) was added
  3. temperatureto cool to ambient temperature
  4. additionthe mixture was diluted with ethyl acetate
  5. customthen partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7f340d2d8807495889390fc5529bf128
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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