Methyl vinyl ketone → (E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one

HRID 523078노트

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HRID 523078 반응식
[NH2:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([Br:9])[CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[CH:41]([C:43]([CH3:45])=[O:44])=[CH2:42]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([Br:9])[N:5]=[CH:6][C:7]=1/[CH:42]=[CH:41]/[C:43](=[O:44])[CH3:45]

참가 물질

7

반응물 4

HCID 6570Methyl vinyl ketoneHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 601457042-Bromo-5-iodopyridin-4-amine

생성물 1

HCID 89995621(E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one수율 78.8%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

4-Amino-2-bromo-5-iodopyridine (4.49 g 15 mmol), tri-o-tolylphosphine (363 mg 1.2 mmol) and palladium acetate (135 mg 0.60 mmol) were dissolved in DMF (45 mL) and di-isopropylethylamine (3.76 mL, 21.6 mmol) and methyl vinyl ketone (2.45 mL, 30 mmol) were added. The reaction was placed under nitrogen and heated at 80° C. for 70 minutes. The reaction was cooled and concentrated in vacuo. Ethyl acetate (150 mL) was added and the solution was washed with water (80 mL). The organic layer was collected, washed with water (2×60 mL) brine, dried over sodium sulfate and concentrated in vacuo. The residue was triturated with ether (2×10 mL) to afford the title compound (2.85 g, 78%).

후처리

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate (150 mL) was added
  4. washthe solution was washed with water (80 mL)
  5. customThe organic layer was collected
  6. washwashed with water (2×60 mL) brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether (2×10 mL)

출처 및 근거

ORD 기록
ord-39c8a259e15245b1893146337a1fccc5
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334286B2

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