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

HRID 2060856노트

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HRID 2060856 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1.[CH3:21]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:21][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 594013876-(1-Chloroisoquinolin-4-yloxy)nicotinonitrile

생성물 1

HCID 594012876-(1-Methylisoquinolin-4-yloxy)nicotinonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 6-(1-chloroisoquinolin-4-yloxy)nicotinonitrile (Preparation 17) (300 mg, 1.1 mmol) in DMF (8 mL) under argon was added trimethylboroxine (148 μL, 1.1 mmol) followed by K2CO3 (442 mg, 3.2 mmol) and palladium tetrakistriphenylphosphine (123 mg, 0.1 mmol). The mixture was purged with argon for 5 min and then heated to 80° C. for 16 h. Solvent was removed in vacuo. The residue was partitioned between EtOAc (100 mL) and water (40 mL), the organic phase was washed with water (40 mL), NaHCO3 (40 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (2% MeOH: DCM) to give the title compound: RT=2.40 min; m/z (ES+)=262.4 [M+H]+.

후처리

  1. customThe mixture was purged with argon for 5 min
  2. customSolvent was removed in vacuo
  3. customThe residue was partitioned between EtOAc (100 mL) and water (40 mL)
  4. washthe organic phase was washed with water (40 mL), NaHCO3 (40 mL), brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo
  7. customthe residue purified by column chromatography (2% MeOH: DCM)

출처 및 근거

ORD 기록
ord-61ff624063f54ad3a618cb99ab98a386
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278442B2

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