Water → 2-[4-(1-Isopropyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

HRID 33861

반응식

HRID 33861 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[N:10][NH:9][C:8]=2[C:12]2[CH:29]=[CH:28][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:37]([CH3:39])[CH3:38].O>CN(C)C=O>[CH:37]([N:10]1[CH:11]=[C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:28][CH:29]=2)=[N:9]1)([CH3:39])[CH3:38]

참가 물질

6

반응물 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 116105532-((4-(4-pyridin-4-yl-1H-pyrazol-3-yl)phenoxy)methyl)quinoline

생성물 1

HCID 115318622-[4-(1-Isopropyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-phenoxymethyl]-quinoline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-[4-(4-Pyridin-4-yl-2H-pyrazol-3-yl)-phenoxymethyl]-quinoline (0.075 g) in dimethyl formamide (2 ml) was added cesium carbonate (0.098 g) and 2-iodo propane (0.030 ml) and the reaction mixture heated at 60° C. for 72 h. The reaction mixture was poured into water and extracted with methylene chloride, dried magnesium sulfate, filtered and concentrated. Purification via Prep TLC eluting with 2% methanol/1% saturated ammonium hydroxide/67% ethyl acetate/30% hexane provided the title compound (60 mg). 1H NMR (400 MHz, CDCl3) δ 8.43 (d, J=6.2 Hz, 2 H), 8.16 (d, J=8.7 Hz, 1 H), 8.05 (d, J=9.1 Hz, 1 H), 7.80 (d, J=8.3 Hz, 1H), 7.70 (m, 1H), 7.65 (d, J=8.7 Hz, 1 H), 7.59 (s, 1H), 7.53 (t, J=7.1 Hz, 1 H), 7.38 (d, J=9.1 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H), 6.99 (d, J=8.7 Hz, 2H), 5.38 (s, 2H) 4.51 (m, 1H), 1.54 (d, J=6.6 Hz, 6H); MS: (M+H m/z=421.2).

후처리

  1. extractionextracted with methylene chloride, dried magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification via Prep TLC
  5. washeluting with 2% methanol/1% saturated ammonium hydroxide/67% ethyl acetate/30% hexane

출처 및 근거

ORD 기록
ord-0e6529db5c13437b8470e62da45a5abf
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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