Sodium Carbonate → HCID 57438770, compound

HRID 2233106Notes

Reaction equation

HRID 2233106 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.[C:37](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:38].C(B1OC(C)(C)C(C)(C)O1)=C>O.O1CCOCC1>[CH2:37]([C:2]1[N:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1)[CH3:38]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 44558591Tri-t-butylphosphine fluoroborateHCID 57438771HCID 57438771, compound

Product 1

HCID 57438770HCID 57438770, compoundYield 625.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

6-Chloro-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine, (Example #F.1.34, 0.25 g, 0.27 mmol), tris(dibenylideneacetone)dipalladium(0) (0.0306 g, 0.034 mmol), sodium carbonate (0.213 g, 2.0 mmol), and tri-t-butylphosphine tetrafluoroborate (Strem, 0.0194 g, 0.07 mmol) were combined in water (0.645 mL) and dioxane (3.35 mL). The reaction was degassed with nitrogen and vinylboronic acid pinacol ester (0.227 mL, 1.34 mmol) was added and the reaction heated at about 95° C. overnight. The reaction was poured onto a pad of silica gel and eluted with EtOAc. The EtOAc solution was washed with brine, dried over sodium sulfate, and concentrated. Ethanol (7.5 mL), EtOAc (7.5 mL), and 10% palladium on carbon (0.050 g) were added. The reaction was purged with hydrogen and stirred under a balloon of hydrogen for about 4 h. The reaction was filtered and concentrated. The residue was purified by FCC using 1:1 EtOAc/heptane and then triturated with heptane to provide the title compound (0.16 g, 65%) on drying: LC/MS (Table 1, Method b) Rt=2.52 min; MS m/z: 366.3 (M+H)+.

Workup

  1. additionwas added
  2. additionThe reaction was poured onto a pad of silica gel
  3. washeluted with EtOAc
  4. washThe EtOAc solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. additionEthanol (7.5 mL), EtOAc (7.5 mL), and 10% palladium on carbon (0.050 g) were added
  8. customThe reaction was purged with hydrogen
  9. filtrationThe reaction was filtered
  10. concentrationconcentrated
  11. customThe residue was purified by FCC
  12. customtriturated with heptane

Sources & evidence

ORD record
ord-7e82da44ddf64d89b8c0eff6ea539bdc
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

Loading…