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Acetonitrile → 3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-5-phenylpyrazin-2-amine

HRID 2373168
ノート
印刷プレビュー

反応式

HRID 2373168 の反応式
Br[C:2]1[N:3]=[C:4]([C:9]2[N:10]([CH2:18][CH3:19])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:18]([N:10]1[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:17]=[C:9]1[C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1)[CH3:19]
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 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

生成物 1

HCID 598524123-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-5-phenylpyrazin-2-amine収率 23.7%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 962Water溶媒

実験手順

5-Bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.038 g, 0.12 mmol) (see Example 2), phenyl boronic acid (0.034 g, 0.27 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.009 g, 0.012 mmol), potassium carbonate (0.045 g, 0.32 mmol), and an 8:1 mixture of acetonitrile:water (3 mL) were combined and subjected to 150° C. for 5 minutes in a SmithSynthesizer microwave. The resulting heterogeneous, black mixture was filtered through a celite pad, which was then washed with ethyl acetate and water. The mixture is extracted into ethyl acetate (×3) and washed with water and saturated sodium chloride. The combined organic layers are dried over magnesium sulfate, filtered and concentrated. The residue is purified on silica, eluting with 2.5% methanol in chloroform to afford the title compound (0.009 g, 23%).

後処理

  1. filtrationThe resulting heterogeneous, black mixture was filtered through a celite pad, which
  2. washwas then washed with ethyl acetate and water
  3. extractionThe mixture is extracted into ethyl acetate (×3)
  4. washwashed with water and saturated sodium chloride
  5. dry with materialThe combined organic layers are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified on silica
  9. washeluting with 2.5% methanol in chloroform

出典と根拠

ORDレコード
ord-e4d211eb2d4f4e7e94e8b36b9ac1bd4a
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07459454B2

反応ノート

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