Cesium carbonate → 1-[(6-chloropyridin-2-yl)methyl]pyridin-2(1H)-one

HRID 1360129ノート

反応式

HRID 1360129 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Cl)[N:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Cl:1][C:2]1[N:3]=[C:4]([CH2:8][N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[O:10])[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 155744402-Chloro-6-(chloromethyl)pyridineHCID 178516071HCID 178516071、化合物

生成物 1

HCID 574257801-[(6-chloropyridin-2-yl)methyl]pyridin-2(1H)-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To the solution of 2-chloro-6-chloromethylpyridine (1.62 g g, 10 mmol) in DMF (10 mL) was added 2-hydroxypyridine (0.95 g, 10 mmol) and Cs2CO3 (6.52 g, 20 mmol). The mixture was stirred overnight, then diluted with water and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (2-4% MeOH in CH2Cl2) to give 1-[(6-chloropyridin-2-yl)methyl]pyridin-2(1H)-one. 1H-NMR (500 MHz, CDCl3) δ 7.62 (t, 1H, J=7.8), 7.51 (dd, 1H, J=6.8, 2.0), 7.31-7.37 (m, 2H), 7.25 (d, 1H, 3=8.3), 6.59 (d, 1H, J=9.2), 6.21 (td, 1H, J=6.6, 1.3), 5.19 (s, 2H). LRMS m/z (M+H) Calcd: 221.7. found: 221.0.

後処理

  1. extractionextracted with CH2Cl2
  2. customThe combined organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customThe solid was purified by silica gel chromatography (2-4% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-4e295eaabe0a40219a8d95464e765496
出典データセット
uspto-grants-2011_02
特許番号
US07879839B2

反応ノート

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