Potassium Carbonate → 1-[2-(3-ethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 2079843Notes

Reaction equation

HRID 2079843 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]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=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]([C:19]1[CH:24]=[C:23]([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:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 16427138(3-Ethylphenyl)boronic acidHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 578292271-[2-(3-ethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-oneYield 50%

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 (152 mg, 0.54 mmol), 3-ethylphenylboronic acid (89 mg, 0.59 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (35 mg, 0.042 mmol), and K2CO3 (186 mg, 1.34 mmol). Dioxane (4 ml) and water (1 ml) were added, and the tube was microwaved at 150° C. for 45 min. The reaction mixture was filtered through a plug of celite. The filtrate was collected and 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 silica gel chromatography using 20-50% EtOAc in hexanes as eluant provided 82 mg (50%) of 1-[2-(3-ethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow solid. MP 199-200.1° C., M+H=308.

Workup

  1. customthe tube was microwaved at 150° C. for 45 min
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. customThe filtrate was collected
  4. custompartitioned between EtOAc/water
  5. customThe organic layers were collected
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customgiving a dark brown solid
  10. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1856803a8b3b4ecfb5941bc3a58df200
Source dataset
uspto-grants-2011_04
Patent number
US07932254B2

Reaction notes

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