Potassium Carbonate → HCID 44553617, 화합물

HRID 714393노트

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HRID 714393 반응식
[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([C:24]2[CH:29]=[CH:28][NH:27][C:26](=[O:30])[CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[CH2:1]([NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:27]2[CH:28]=[CH:29][C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:25][C:26]2=[O:30])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 5987864-Phenylpyridin-2-olHCID 15115857N-benzyl-2-chloropyridine-4-carboxamide

생성물 1

HCID 44553617HCID 44553617, 화합물수율 28.8%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

A degassed mixture of N-benzyl-2-chloroisonicotinamide (0.25 g, 1.01 mmol), 4-phenylpyridin-2(1H)-one (0.17 g, 0.91 mmol), potassium carbonate (0.20 g, 1.44 mmol), 8-hydroxyquiniline (0.02 g, 0.14 mmol) and copper(I) iodide (0.03 g, 0.14 mmol) in N,N-dimethylformamide (3.0 mL) was heated at 130° C. for 18 hours. The resulting solution was cooled to ambient temperature, quenched with ammonium hydroxide solution (10 mL) and extracted with ethyl acetate (2×25 mL). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give N-benzyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)isonicotinamide as a colorless solid (0.10 g, 25%): mp 162-163° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.43 (t, J=5.1 Hz, 1H), 8.73 (d, J=5.1 Hz, 1H), 8.24, (s, 1H), 7.99 (d, J=7.3 Hz, 1H), 7.89 (d, J=5.1 Hz, 1H), 7.79-7.76 (m, 2H), 7.54-7.45 (m, 3H), 7.36-7.18 (m, 5H), 6.82 (s, 1H), 6.76 (d, J=7.3 Hz, 1H), 4.48 (d, J=5.7 Hz, 2H); 13C NMR (75 MHz, DMSO-d6) δ 164.2, 161.6, 152.7, 152.0, 150.2, 143.6, 139.4, 137.4, 136.6, 130.5, 129.6, 128.8, 127.9, 127.4, 127.3, 121.6, 119.9, 116.8, 105.6, 43.3; MS (ES+) m/z 382.6 (M+1).

후처리

  1. temperatureThe resulting solution was cooled to ambient temperature
  2. customquenched with ammonium hydroxide solution (10 mL)
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-5b63f159e6834ec7816367e7b102b485
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187426B2

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