Hydrochloric Acid → 2-(4-chlorophenyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1639579Notes

Reaction equation

HRID 1639579 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.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].C(#N)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[N:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 580017002-(4-chlorophenyl)-5H-pyrrolo[2,3-b]pyrazineYield 61.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave tube containing 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1, 0.165 g, 0.833 mmol), 4-chlorophenylboronic acid (6, 0.118 g, 0.757 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.028 g, 0.038 mmol), 1.5 mL of acetonitrile and 1.5 mL of 1.00 M potassium carbonate in water were added. The resulting mixture was heated at 120° C. in the microwave for 10 minutes. The reaction was poured into 1M aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 1% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (7, 107 mg). MS (ESI) [M+H+]+=229.8.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. custompurified by silica gel column chromatography
  8. washeluting with 1% methanol in dichloromethane
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aa6fc4b16a534e3d8bdb31f0a67dbc5b
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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