Potassium Carbonate → 2-[4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenoxymethyl]-quinoline

HRID 1170314

반응식

HRID 1170314 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1>CC(C)=O.[Cl-].[Na+].O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)=[CH:14][CH:13]=3)[N:10]=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 685764624-(5-Pyridin-4-yl-pyrazol-1-yl)-phenol

생성물 1

HCID 116608572-[4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenoxymethyl]-quinoline수율 69.6%

시약·촉매·용매 2

HCID 180Acetone용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
60 °C

실험 절차

To a solution of 4-(5-Pyridin-4-yl-pyrazol-1-yl)-phenol (82 mg) in acetone was added potassium carbonate (153 mg) and 2-Chloromethyl-quinoline (95 mg) and the reaction mixture heated at 60° C. for 18 h. The reaction mixture was poured into brine and extracted with ethyl acetate, dried magnesium sulfate, filtered and concentrated. Purification via combiflash MPLC provided the title compound (91 mg). 1H NMR (400 MHz, CDCl3) δ 8.51 (m, 2H), 8.20 (d, J=8.7 Hz, 1H), 8.06 (d, J=8.7 Hz, 1H), 7.83 (d, J=7.1 Hz, 1H), 7.74 (m, 2H), 7.65 (d, J=8.7 Hz, 1H), 7.57 (m, 1H), 7.20 (d, J=8.7 Hz, 2H), 7.09 (d, J=5.8 Hz, 2H), 7.02 (d, J=9.1 Hz, 2H), 6.60 (d, J=1.7 Hz, 1H), 5.39 (s, 2H); MS: (M+H m/z=379.0).

후처리

  1. extractionextracted with ethyl acetate, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via combiflash MPLC

출처 및 근거

ORD 기록
ord-836547c216364c8880f9567c6fbc831e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825254B2

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