1,10-Phenanthroline → 4-Methoxy-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

HRID 33907

反応式

HRID 33907 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)=[CH:23][N:22]([CH3:31])[N:21]=3)=[CH:16][CH:15]=2)[CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:46](=O)([O-])[O-:47].[Cs+].[Cs+]>CO.[Cu](I)I>[CH3:46][O:47][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)=[CH:23][N:22]([CH3:31])[N:21]=3)=[CH:16][CH:15]=2)[CH:3]=1

参加物

6

反応物 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 115970894-Chloro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

生成物 1

HCID 116042034-Methoxy-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline収率 59.8%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 887Methanol溶媒

反応条件

温度
165 °C

実験手順

To a solution of 4-Chloro-2-[4-(1-methyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline (125 mg) in methanol (4 mL) was added phenanthroline (78 mg), cesium carbonate (143 mg) and copper iodide (5 mg). The reaction mixture was heated in a microwave reactor at 165° C. with 50 W of power for 20 min. The reaction mixture was filtered through celite and concentrated. Purification via MPLC biotage chromatography, eluting with 5% methanol/1% ammonium hydroxide/methylene chloride provided the title compound (74 mg). 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=5.4 Hz, 2 H), 8.18 (d, J=8.3 Hz, 1H), 7.97 (d, J=8.3 Hz, 1H), 7.68 (m, 1H), 7.55 (s, 1H), 7.49 (t, J=7.1 Hz, 1 H), 7.37 (d, J=9.1, Hz, 2 H), 7.15 (d, J=6.2 Hz, 2H), 7.01 (m, 3H), 5.32 (s, 2H), 4.02 (s, 3 H), 3.95 (s, 3H); MS: (M+H m/z=423.3).

後処理

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. customPurification via MPLC biotage chromatography
  4. washeluting with 5% methanol/1% ammonium hydroxide/methylene chloride

出典と根拠

ORDレコード
ord-e428d317c60849d8b0a9f8a1a2b2cb51
出典データセット
uspto-grants-2008_09
特許番号
US07429665B2

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