Sodium Carbonate → HCID 90105361, compound

HRID 1049880Notes

Reaction equation

HRID 1049880 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[N:11]1[CH:16]=[CH:15][C:14]([C:2]2[N:3]=[C:4]3[CH:5]=[CH:6][NH:7][C:8]3=[N:9][CH:10]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 90105361HCID 90105361, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 10 mL microwave vial was charged with 5-bromo-4,7-diazaindole (0.471 g, CASRN 875781-43-4), 4-pyridylboronic acid (0.58 g), 1M Na2CO3 (3 mL), 1,1′-(dppf)Pd(II)Cl2 (0.097 g) and MeCN (3 mL), capped and irradiated in a microwave reactor at 150° C. for 30 min. The reaction was cooled and partitioned between H2O and EtOAc. The aqueous layer was twice washed with EtOAc. The combined organic layers were washed once with brine, dried (MgSO4), filtered and concentrated to afford a solid residue. The crude purified by SiO2 chromatography eluting with an EtOH/EtOAc gradient (1 to 20% EtOH over 12 min) to afford 0.28 g of pure 2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin (22).

Workup

  1. customcapped
  2. customirradiated in a microwave reactor at 150° C. for 30 min
  3. temperatureThe reaction was cooled
  4. custompartitioned between H2O and EtOAc
  5. washThe aqueous layer was twice washed with EtOAc
  6. washThe combined organic layers were washed once with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford a solid residue
  11. customThe crude purified by SiO2 chromatography
  12. washeluting with an EtOH/EtOAc gradient (1 to 20% EtOH over 12 min)

Sources & evidence

ORD record
ord-a21626777d9e4a41bb2a0c68316f1959
Source dataset
uspto-grants-2016_07
Patent number
US09382257B2

Reaction notes

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