Potassium Carbonate → HCID 44208110, compound

HRID 1677529Notes

Reaction equation

HRID 1677529 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:23]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:25]=1)[CH3:18].C([O-])([O-])=O.[K+].[K+].O1CCOCC1>O>[CH2:17]([O:19][C:20]1[CH:25]=[C:24]([C:2]2[N:3]=[C:4]3[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)[CH:23]=[C:22]([N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:21]=1)[CH3:18]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-oneHCID 59541063HCID 59541063, compound

Product 1

HCID 44208110HCID 44208110, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A microwave flask was charged with 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (48 mg, 0.17 mmol), 1-[3-ethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyrrolidine (54 mg, 0.17 mmol), and K2CO3 (59 mg, 0.43 mmol). Dioxane (2.1 ml) and water (0.5 ml) were added, and the solution was vacuum degassed under argon. [1,1′-Bis(diphenylphosphino)ferrocene]palladium(ll) dichloride dichloromethane complex (14 mg, 0.02 mmol) was added, and the reaction mixture was heated (150° C.) in a microwave reactor for 45 minutes. The reaction mixture was filtered through a plug of celite using ethyl acetate. The filtrate was transferred to a separatory funnel and shaken with water (20 ml). The organic phase was collected and the aqueous phase back extracted with ethyl acetate (2×15 ml). The organic phases were combined, dried (MgSO4), filtered and stripped to provide a viscous semi-solid. This material was purified by preparative TLC, eluting with 4.8% methanol in methylene chloride to afford 31 mg of 1-[2-(3-ethoxy-5-pyrrolidin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow powder. MP 236-237° C., M+H=393.

Workup

  1. customdegassed under argon
  2. addition[1,1′-Bis(diphenylphosphino)ferrocene]palladium(ll) dichloride dichloromethane complex (14 mg, 0.02 mmol) was added
  3. filtrationThe reaction mixture was filtered through a plug of celite
  4. customThe filtrate was transferred to a separatory funnel
  5. customThe organic phase was collected
  6. extractionthe aqueous phase back extracted with ethyl acetate (2×15 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customto provide a viscous semi-solid
  10. customThis material was purified by preparative TLC
  11. washeluting with 4.8% methanol in methylene chloride

Sources & evidence

ORD record
ord-74e61c39cb6248f7acdd4fb950bb230d
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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