Potassium Carbonate → 6-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

HRID 2060855노트

반응식

HRID 2060855 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][N:3]=1.Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 42818821-Chloro-4-hydroxyisoquinolineHCID 51520946-Chloro-3-pyridinecarbonitrile

생성물 1

HCID 594013876-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 1-chloro-4-hydroxyisoquinoline (1.0 g, 5.6 mmol) in DMF (16 mL), was added 6-chloronicotinonitrile (0.55 g, 4.0 mmol) and K2CO3 (1.65 g, 11.9 mmol). The reaction mixture was heated at 70° C. for 6.5 h. Solvent was removed in vacuo and residue partitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL). The organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=3.66 min; m/z (ES+)=282.0 [M+H]+.

후처리

  1. customSolvent was removed in vacuo and residue
  2. custompartitioned between EtOAc (100 mL), THF (100 mL) and water (60 mL)
  3. washThe organic phase was washed with water (2×60 mL), 1M NaOH (2×40 mL), brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo

출처 및 근거

ORD 기록
ord-3c4ff8d0135045eaab7945089e091a7a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278442B2

반응 노트

불러오는 중…