Sodium Carbonate → HCID 90105361, 화합물

HRID 1049880노트

반응식

HRID 1049880 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 90105361HCID 90105361, 화합물수율 60%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a21626777d9e4a41bb2a0c68316f1959
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382257B2

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