Sodium Carbonate → 5-(1-phenyl-1H-1,3-benzodiazol-5-yl)-1-[3-(piperidin-1-yl)propyl]-1,2-dihydropyridin-2-one

HRID 1275552노트

반응식

HRID 1275552 반응식
I[C:2]1[CH:3]=[CH:4][C:5](=[O:17])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=1.[C:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31](B4OC(C)(C)C(C)(C)O4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1.O>[C:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:2]4[CH:3]=[CH:4][C:5](=[O:17])[N:6]([CH2:8][CH2:9][CH2:10][N:11]5[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]5)[CH:7]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 120181725-iodo-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-oneHCID 120181731-Phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-benzoimidazole

생성물 1

HCID 53294085-(1-phenyl-1H-1,3-benzodiazol-5-yl)-1-[3-(piperidin-1-yl)propyl]-1,2-dihydropyridin-2-one수율 71%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

5-iodo-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (18) (0.096 g, 0.28 mmol), 1-phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-benzoimidazole (0.081 g, 0.25 mmol), palladium(II) acetate (0.003 g, 0.013 mmol), triphenylphosphine (0.010 g, 0.038 mmol) and sodium carbonate (0,080 g, 0.75 mmol) were stirred in 1.6 mL of a 3:1 mixture of dioxane/water. The mixture was degassed 3x by alternating vacuum and an argon atmosphere. The reaction was heated to 80° C. for 18 h, cooled and diluted with water. The aqueous phase was extracted 3x with EtOAc and the resulting organic phase was dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (eluted with 85:15 CH2Cl2 /MeOH) afforded 0.073 g 5-(1-phenyl-1H-benzoimidazol-5-yl)-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (19) (71% yield). 1H NMR (CDC13) o 9.60 (s, 1H), 7.90 (d, J=1.3 Hz, 1H), 7.74-7.67 (m, 2H), 7.64-7.48 (m, 6H), 7.39 (dd, J=2.5, 9.5 Hz, 1H), 6.68 (d, J=9.5 Hz, 1H), 4.13 (t, J=6.5 Hz, 2H), 2.42 (bs, 6H), 2.10 (t, J=6.5 Hz, 2H), 1.64 (m, 4H), 1.46 (m, 2H). Mass Spectrometry (for C26H28N4O): [M+H]+413.2334, theoretical 413.2336. ##STR28##

후처리

  1. customThe mixture was degassed 3x
  2. temperaturecooled
  3. additiondiluted with water
  4. extractionThe aqueous phase was extracted 3x with EtOAc
  5. dry with materialthe resulting organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washby flash column chromatography (eluted with 85:15 CH2Cl2 /MeOH)

출처 및 근거

ORD 기록
ord-0d56e135287f4436afccf9856debe137
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162804

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