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

HRID 1170314ノート

反応式

HRID 1170314 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-836547c216364c8880f9567c6fbc831e
出典データセット
uspto-grants-2010_11
特許番号
US07825254B2

反応ノート

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