Potassium Phosphate, Tribasic → HCID 10110424, compound

HRID 895148Notes

Reaction equation

HRID 895148 reaction equation
Br[C:2]1[N:6]2[CH:7]=[N:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:5]2=[N:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][C:25]=1[C:39]1[C:40]([C:45]#[N:46])=[CH:41][CH:42]=[CH:43][CH:44]=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:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:6]3[CH:7]=[N:8][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:26][C:25]=1[C:39]1[C:40]([C:45]#[N:46])=[CH:41][CH:42]=[CH:43][CH:44]=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 22385760HCID 22385760, compound

Product 1

HCID 10110424HCID 10110424, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 3-bromo-7-trifluoromethylimidazo[1,2-c]pyrimidine (100 mg, 0.375 mmol), dried potassium phosphate (0.159 g, 0.750 mmol) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (0.2424 g, 0.750 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was degassed by evacuation and refilling with nitrogen three times. Tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.019 mmol) was then added and the mixture was degassed with two more evacuation-refilling cycles before heating at 80° C. under nitrogen for 3 h. The mixture was partitioned between ethyl acetate (250 ml) and brine (250 ml), and the aqueous layer was extracted further with ethyl acetate (250 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 40% EtOAc/isohexane), then recrystallisation (EtOAc) to give 6.8 mg (5%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.46 (1H, t, J 8.6 Hz), 7.56 (1H, td, J 7.7, 1.3 Hz), 7.60 (1H, m), 7.65-7.74 (3H, m), 7.85 (1H, dd, J 7.8, 1.6 Hz), 7.89 (1H, s), 7.99 (1H, s), 9.37 (1H, s); MS (ES+) m/z 383 [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. customThe mixture was partitioned between ethyl acetate (250 ml) and brine (250 ml)
  4. extractionthe aqueous layer was extracted further with ethyl acetate (250 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography (silica gel, 40% EtOAc/isohexane)
  8. customrecrystallisation (EtOAc)

Sources & evidence

ORD record
ord-a22f2195a4934042ac355cb13a3dfcba
Source dataset
uspto-grants-2005_07
Patent number
US06914065B2

Reaction notes

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