Sodium Carbonate → HCID 90105361、化合物

HRID 1049880ノート

反応式

HRID 1049880 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 90105361HCID 90105361、化合物収率 60%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a21626777d9e4a41bb2a0c68316f1959
出典データセット
uspto-grants-2016_07
特許番号
US09382257B2

反応ノート

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