Cesium carbonate → HCID 53247622, compound

HRID 1628125Notes

Reaction equation

HRID 1628125 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:24])[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.C([O:27][C:28]([CH2:30][N:31]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32]1)=[O:29])C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[CH3:24][C:4]1[N:5]2[C:10]3[CH:11]=[CH:12][NH:13][C:9]=3[N:8]=[CH:7][C:6]2=[C:2]([C:34]2[CH:33]=[N:32][N:31]([CH2:30][C:28]([OH:29])=[O:27])[CH:35]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 58382162HCID 58382162, compoundHCID 67076146HCID 67076146, compound

Product 1

HCID 53247622HCID 53247622, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

3-Bromo-1-methyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine (0.356 g, 0.878 mmol) (Preparation #AB.1), 1-(ethoxycarbonylmethyl)-1H-pyrazole-4-boronic acid, pinacol ester (0.295 g, 1.05 mmol), and Cs2CO3 (0.1716 g, 2.20 mmol) were combined in 1,4-dioxane (7.0 mL) and water (1.8 mL). The mixture was degassed by bubbling N2 directly into the mixture. After about 10 min, PdCl2(PPh3)2 (0.043 g, 0.061 mmol) was added and degassing continued for about 5 more min. The mixture was heated at about 85° C. for about 16 h. Aqueous NaOH (1 N, 3 mL) was added and heating continued for about 2 h. The mixture was allowed to cool to rt and aqueous HCl (1 N, 10 mL) was added. The mixture was concentrated in vacuo to give 2-(4-(1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)-1H-pyrazol-1-yl)acetic acid: LCMS (Table 2, Method b) Rt=1.37 min.; MS m/z: 297 (M+H)+

Workup

  1. customThe mixture was degassed
  2. customby bubbling N2 directly into the mixture
  3. customdegassing
  4. additionAqueous NaOH (1 N, 3 mL) was added
  5. temperatureheating
  6. waitcontinued for about 2 h
  7. temperatureto cool to rt
  8. additionaqueous HCl (1 N, 10 mL) was added
  9. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-daafb5d73f884e1492195321fdc4ce4d
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…