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Potassium Carbonate → 3-Phenyl-2-p-tolylpyrido[2,3-b]pyrazine

HRID 517923
ノート
印刷プレビュー

反応式

HRID 517923 の反応式
Cl[C:2]1[N:3]=[C:4]2[CH:17]=[CH:16][CH:15]=[N:14][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.B(O)(O)[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=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>[C:8]1([C:7]2[N:6]=[C:5]3[N:14]=[CH:15][CH:16]=[CH:17][C:4]3=[N:3][C:2]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=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 79799Tolylboronic acidHCID 866818582-Chloro-3-phenylpyrido[2,3-b]pyrazine

生成物 1

HCID 590904003-Phenyl-2-p-tolylpyrido[2,3-b]pyrazine

試薬・触媒・溶媒 3

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

実験手順

2-Chloro-3-phenylpyrido[2,3-b]pyrazine (step 3) (175 mg, 0.724 mmol) in dry dioxane (4 ml) under nitrogen was treated with p-tolylboronic acid (108 mg, 0.797 mmol), potassium carbonate (200 mg, 1.448 mmol) in water (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (41.8 mg, 0.036 mmol). The resulting mixture was heated using microwave radiation at 150° 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 in iso-hexane to afford the titled compound as a yellow solid;

後処理

  1. temperatureThe resulting mixture was heated
  2. customat 150° 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 in iso-hexane

出典と根拠

ORDレコード
ord-7c980118dfca49468da63a7db8bb95f2
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09115129B2

反応ノート

読み込み中…

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