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Potassium Phosphate, Tribasic → HCID 10156779, compound

HRID 586225
Notes
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Reaction equation

HRID 586225 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.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[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:26][C:25]=1[C:39]1[C:40]([C:45]#[N:46])=[CH:41][CH:42]=[CH:43][CH:44]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 10156779HCID 10156779, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (99.0 mg, 0.371 mmol), dried potassium phosphate (0.1581 g, 0.745 mmol) and 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (0.2402 g, 0.743 mmol) in anhydrous N,N-dimethylacetamide (2 ml) was degassed by evacuation and refilling with nitrogen three times. Tetrakis(triphenylphosphine)palladium(0) (22.1 mg, 0.0191 mmol) was then added and the mixture was degassed with two more evacuation-refilling cycles before heating at 80° C. under nitrogen for 6.5 h. The mixture was diluted with ethyl acetate and filtered through glass fibre paper, washing the solid with more ethyl acetate. The filtrates were washed with brine (15 ml), and the aqueous layer was extracted further with ethyl acetate (25 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 30% EtOAc/isohexane) to give 76.6 mg (54%) of the title compound: mp 168-174° C. (CH2Cl2-EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.43 (1H, t, J 9.0 Hz), 7.57 (1H, td, J 7.8, 1.2 Hz), 7.60 (1H, d, J 7.8 Hz), 7.73 (1H, td, J 7.8, 1.3 Hz), 7.85 (1H, dd, J 7.7, 1.1 Hz), 8.16-8.23 (2H, m), 8.62 (1H, s), 8.81 (1H, s); MS (ES+) m/z 384 [M+H]+. Anal. Found: C, 58.31; H, 2.28; N, 17.74%. Required for C19H9F4N5.0.5H2O: C, 58.17; H, 2.57; N, 17.85%.

Workup

  1. customwas degassed by evacuation and refilling with nitrogen three times
  2. customthe mixture was degassed with two more evacuation-refilling cycles
  3. additionThe mixture was diluted with ethyl acetate
  4. filtrationfiltered through glass fibre paper
  5. washwashing the solid with more ethyl acetate
  6. washThe filtrates were washed with brine (15 ml)
  7. extractionthe aqueous layer was extracted further with ethyl acetate (25 ml)
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (silica gel, 30% EtOAc/isohexane)

Sources & evidence

ORD record
ord-c8fdd85671fe4b91a68d1500bff27bc2
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936608B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes