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

HRID 1360129노트

반응식

HRID 1360129 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4e295eaabe0a40219a8d95464e765496
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879839B2

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