Potassium Carbonate → HCID 59540852, compound

HRID 1677440Notes

Reaction equation

HRID 1677440 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](B(O)O)[CH:23]=[CH:24][CH:25]=1)[CH3:18].C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].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]=[CH:22][CH:21]=1)[CH3:18]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27739203-Ethoxybenzeneboronic acidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 59540852HCID 59540852, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Procedure

A microwave tube was charged with 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (146 mg, 0.52 mmol), 3-ethoxybenzeneboronic acid (94 mg, 0.57 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (34 mg, 0.041 mmol), and K2CO3 (179 mg, 1.30 mmol). Dioxane (4 ml) and water (1 ml) were added, and the tube was microwaved at 150° C. for 30 min. The reaction mixture was partitioned between EtOAc/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a dark brown solid. The crude product was purified by preparative thin layer chromatography (70% EtOAc/Hexane) as eluant to provide 120 mg (72%) of 1-[2-(3-ethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid. MP 195-196° C., M+H=324.

Workup

  1. customthe tube was microwaved at 150° C. for 30 min
  2. customThe reaction mixture was partitioned between EtOAc/water
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving a dark brown solid
  8. customThe crude product was purified by preparative thin layer chromatography (70% EtOAc/Hexane) as eluant

Sources & evidence

ORD record
ord-e4a04787be9241769543f317f4f676e9
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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