Water → HCID 57438740, compound

HRID 2233079Notes

Reaction equation

HRID 2233079 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.O.C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.[C:30](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:31]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:3]3[C:2]([CH:30]=[CH2:31])=[N:7][CH:6]=[CH:5][N:4]3[CH:8]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 44558591Tri-t-butylphosphine fluoroborateHCID 574387418-Chloro-2-(4-fluorophenyl)imidazo[1,2-A]pyrazine

Product 1

HCID 57438740HCID 57438740, compoundYield 642.6%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 8-chloro-2-(4-fluorophenyl)-imidazo[1,2-a]pyrazine (Example #6, Step A, 3.96 g, 16 mmol) in dioxane (80 mL) was added water (15.4 mL), sodium carbonate (EM Science, 5.08 g, 48 mmol), tri-t-butylphosphine tetrafluoroborate (Strem, 0.46 g, 1.6 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.73 g, 0.8 mmol). The reaction was degassed with nitrogen and then vinylboronic acid pinacolester (5.44 mL, 32 mmol) was added. The mixture was heated to about 95° C. for about 16 h. The reaction was cooled, EtOAc was added (250 mL), and the mixture was washed with water. The organic layer was dried over sodium sulfate, filtered, and evaporated. The residue was purified by FCC (33%-50% EtOAc/heptane). The residue was triturated with heptane and filtered to yield the title compound as a brown solid (2.46 g, 62%): LC/MS (Table 1, Method b) Rt=2.74 min; MS m/z: 240.3 (M+H)+.

Workup

  1. customThe reaction was degassed with nitrogen
  2. additionvinylboronic acid pinacolester (5.44 mL, 32 mmol) was added
  3. temperatureThe reaction was cooled
  4. additionEtOAc was added (250 mL)
  5. washthe mixture was washed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by FCC (33%-50% EtOAc/heptane)
  10. customThe residue was triturated with heptane
  11. filtrationfiltered

Sources & evidence

ORD record
ord-c81084fa5c8e49cd97f9962520398057
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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