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Potassium Carbonate → 2-Chloro-3-phenylpyrido[2,3-b]pyrazine

HRID 406250
ノート
印刷プレビュー

反応式

HRID 406250 の反応式
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][CH:10]=[N:11][C:5]2=[N:4][C:3]=1Cl.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][CH:10]=[N:11][C:5]2=[N:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 117888682,3-Dichloropyrido[2,3-b]pyrazine

生成物 1

HCID 866818582-Chloro-3-phenylpyrido[2,3-b]pyrazine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water
溶媒
2 回
HCID 312751,4-Dioxane溶媒

実験手順

2,3-Dichloropyrido[2,3-b]pyrazine (step 2) (500 mg, 2.5 mmol) in dry dioxane (10 ml), under nitrogen was treated with phenylboronic acid (305 mg, 2.5 mmol), potassium carbonate (691 mg, 5 mmol) in water (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (144 mg, 0.125 mmol). The resulting mixture was heated using microwave radiation at 100° C. for 1 hour. After cooling to RT, the mixture was diluted with water (100 ml) and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO4 and filtered. The solvent was removed in vacuo and the crude product was purified by chromatography on silica eluting with 0-30% EtOAc/iso-hexane to afford the title compound as a solid;

後処理

  1. temperatureThe resulting mixture was heated
  2. customat 100° C.
  3. customfor 1 hour
  4. extractionextracted with DCM (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe crude product was purified by chromatography on silica eluting with 0-30% EtOAc/iso-hexane

出典と根拠

ORDレコード
ord-388b05f7fc084cfcaef4f7afcf216013
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08754085B2

反応ノート

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