Potassium Phosphate, Tribasic → HCID 9836526, compound

HRID 586237Notes

Reaction equation

HRID 586237 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=1>CN(C)C(=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>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[N:7]=[CH:8][CH:9]=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:22][C:21]=1[C:35]1[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrileHCID 22329553HCID 22329553, compound

Product 1

HCID 9836526HCID 9836526, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 7-bromoimidazo[1,2-b][1,2,4]triazine (0.22 g, 1.105 mmol), dried potassium phosphate (0.425 g, 2.002 mmol) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile (0.649 g, 2.008 mmol) in anhydrous N,N-dimethylacetamide (4 ml) was degassed by evacuation and refilling with nitrogen three times. Tetrakis(triphenylphosphine)palladium(0) (0.058 g, 0.05 mmol) was added and the mixture was degassed with two more evacuation-refilling cycles before heating at 80° C. for 4.5 h. The mixture was cooled to ambient temperature, diluted with ethyl acetate and filtered. The filtrate was washed with brine (200 ml), and the aqueous portion extracted with more ethyl acetate. The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, EtOAc) then recrystallisation (EtOAc) to give 74 mg (24%) of the title compound: mp 211-215° C.; 1H NMR (360 MHz, CDCl3) δ 7.36-7.41 (1H, t, J 7.2 Hz), 7.53-7.61 (2H, m), 7.70-7.74 (1H, m), 7.83 (1H, d, J 7.7 Hz), 8.12-8.16 (2H, m), 8.35 (1H, s), 8.50 (1H, dd, J 2.1, 11.6 Hz); MS (ES+) m/z 316 [M+H]+.

Workup

  1. customwas degassed by evacuation and refilling with nitrogen three times
  2. customthe mixture was degassed with two more evacuation-refilling cycles
  3. temperatureThe mixture was cooled to ambient temperature
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered
  6. washThe filtrate was washed with brine (200 ml)
  7. extractionthe aqueous portion extracted with more ethyl acetate
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography (silica gel, EtOAc)
  11. customrecrystallisation (EtOAc)

Sources & evidence

ORD record
ord-4340d1fbc6344b4783ed487004061b84
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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