Sodium ethoxide → 2-[4-(5-Pyridin-4-yl-pyrimidin-4-yl)-phenoxymethyl]-quinoline

HRID 33835

反応式

HRID 33835 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([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:12][CH:11]=2)=O)=[CH:3][CH:2]=1.Cl.[CH:29]([NH2:31])=[NH:30].[Na].[O-][CH2:34]C.[Na+]>COC(N(C)C)OC.C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:12][CH:11]=3)=[N:30][CH:29]=[N:31][CH:34]=2)=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 336797272-(Pyridin-4-yl)-1-(4-(quinolin-2-ylmethoxy)phenyl)ethan-1-one

生成物 1

HCID 116610912-[4-(5-Pyridin-4-yl-pyrimidin-4-yl)-phenoxymethyl]-quinoline収率 38%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 78373Dimethylformamide dimethyl acetal溶媒

実験手順

2-pyridin-4-yl-1-[4-(quinolin-2-ylmethoxy)-phenyl]-ethanone (200 mg) was heated at reflux in dimethoxymethyl-dimethyl amine (1 ml) for 1 h and concentrated. The crude reaction mixture was dissolved in ethanol (3 ml) and formamidine hydrochloride (90 mg, 2 eq.) was added. In a separate flask sodium (40 mg) was added to ethanol 3 ml and stirred 10 min. The sodium ethoxide solution was added to the reaction mixture and was heated at reflux for 1 h. The reaction mixture was concentrated and purified via Biotage MPLC chromatography on a 25S column eluting with 40-100% ethyl acetate/hexane to provide the title compound (83 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 8.53(m, 3 H), 8.14 (d, J=8.7 Hz, 1H), 8.03 (d, J=8.3 Hz, 1H), 7.79 (d, J=7.9 Hz, 1 H), 7.70 (m, 1 H), 7.58 (d, J=8.7 Hz, 1H), 7.50 (m, 1H), 7.33 (d, J=9.1 Hz, 2H) 7.10 (d, J=6.2, 2H), 6.91(d, J=9.1 Hz, 2H), 5.34 (s, 2H) 2.77 (s, 3H); MS: (M+H m/z=391.2).

後処理

  1. concentrationconcentrated
  2. customThe crude reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux for 1 h
  5. concentrationThe reaction mixture was concentrated
  6. custompurified via Biotage MPLC chromatography on a 25S column
  7. washeluting with 40-100% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-5c3753efd3b3494daa342dfcfb9faec7
出典データセット
uspto-grants-2008_09
特許番号
US07429665B2

関連ノート

読み込み中…