Cesium carbonate → HCID 58382243, compound

HRID 1969662Notes

Reaction equation

HRID 1969662 reaction equation
Br[C:2]1[N:3]=[C:4]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:5]2[C:10]3[CH:11]=[CH:12][N:13](S(C4C=CC(C)=CC=4)(=O)=O)[C:9]=3[N:8]=[CH:7][C:6]=12.[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+].[NH4+].[Cl-]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)Cl.O.CCO>[CH:24]1([C:4]2[N:5]3[C:10]4[CH:11]=[CH:12][NH:13][C:9]=4[N:8]=[CH:7][C:6]3=[C:2]([C:37]3[CH:38]=[CH:39][C:34]([S:31]([CH3:30])(=[O:33])=[O:32])=[CH:35][CH:36]=3)[N:3]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

11

Reactant 5

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 583822553-Bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine

Product 1

HCID 58382243HCID 58382243, compoundYield 41%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
120 °C

Procedure

A microwave vial was charged with 3-bromo-1-cyclohexyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.050 g, 0.11 mmol, Preparation #MM.1), 4-(methylsulfonyl)phenylboronic acid (0.023 g, 0.12 mmol, Acros), cesium carbonate (0.086 g, 0.26 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.0066 g, 0.0000094 mmol), and 1,4-dioxane (0.42 mL), EtOH (0.42 mL), and water (0.21 mL). The vial was capped and the mixture was heated to about 120° C. for about 20 min (5 min ramp time, 300 Watts max power, 250 psi max pressure) in a microwave. The reaction mixture was concd under reduced pressure to give a solid that was dissolved in 1,4-dioxane (1.0 mL) and transferred to a microwave vial. Aqueous 2 N NaOH (0.11 mL, 0.21 mmol) was added and the vial was capped. The solution was heated to about 100° C. for about 15 min in a microwave (300 W max power, 250 psi max pressure, 5 min ramp time). DCM (10 mL) and saturated aqueous NH4Cl (5 mL) were added to the reaction solution. The layers were separated and the aqueous solution was extracted with additional DCM (5 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to give a light brown solid. Upon addition of DCM (1 mL), a yellow precipitate formed that was collected by vacuum filtration and dried overnight on a Buchner funnel to give 1-cyclohexyl-3-(4-(methylsulfonyl)phenyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.017 g, 41%): LC/MS (Table 1, Method a) Rt=2.39 min; MS m/z: 395 (M+H)+.

Workup

  1. customThe vial was capped
  2. customto give a solid
  3. customthe vial was capped
  4. temperatureThe solution was heated to about 100° C. for about 15 min in a microwave (300 W max power, 250 psi max pressure, 5 min ramp time)
  5. customThe layers were separated
  6. extractionthe aqueous solution was extracted with additional DCM (5 mL)
  7. dry with materialThe combined extracts were dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customto give a light brown solid
  11. customa yellow precipitate formed
  12. filtrationthat was collected by vacuum filtration
  13. customdried overnight on a Buchner funnel

Sources & evidence

ORD record
ord-6c3e60a7b2b843a88674ecaca3f1b468
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…