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

HRID 1360129Notes

Reaction equation

HRID 1360129 reaction equation
[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

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 155744402-Chloro-6-(chloromethyl)pyridineHCID 178516071HCID 178516071, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4e295eaabe0a40219a8d95464e765496
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

Loading…